3-Chloro-4-fluorobenzonitrile -Drug Synthesis Database

【结构式】

【分子编号】51277

【品名】3-Chloro-4-fluorobenzonitrile

【CA登记号】117482-84-5

【分子式】C₇H₃ClFN

【分子量】155.5586632

【元素组成】C 54.05% H 1.94% Cl 22.79% F 12.21% N 9%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The N-benzyl indole derivative (III) was prepared by alkylation of 5-(benzyloxy)indole (I) with benzyl bromide (II) in the presence of KOH. The O-benzyl protecting group of (III) was subsequently removed by transfer hydrogenolysis with ammonium formate and Pd/C to afford the 5-hydroxyindole (IV), which was further condensed with 3-chloro-4-fluorobenzonitrile (V) to produce the diaryl ether (VI). Finally, basic hydrolysis of the cyano group of (VI) gave the corresponding benzoic acid.

参考文献中间体

合成目标

【1】 Mase, T.; Inami, H.; Hara, H.; Fujii, M; Oritani, H.; Koutoku, H.; Igarashi, S.; A novel class of inhibitors for human steroid 5alpha-reductase: Synthesis and biological evaluation of indole derivatives. II. Chem Pharm Bull 2000, 48, 3, 382.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	30840	5-Benzyloxyindole; benzyl 1H-indol-5-yl ether; 5-(benzyloxy)-1H-indole	1215-59-4	C₁₅H₁₃NO	详情	详情
(II)	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(III)	51281	benzyl 1-benzyl-1H-indol-5-yl ether; 1-benzyl-5-(benzyloxy)-1H-indole		C₂₂H₁₉NO	详情	详情
(IV)	51282	1-benzyl-1H-indol-5-ol		C₁₅H₁₃NO	详情	详情
(V)	51277	3-Chloro-4-fluorobenzonitrile	117482-84-5	C₇H₃ClFN	详情	详情
(VI)	51283	4-[(1-benzyl-1H-indol-5-yl)oxy]-3-chlorobenzonitrile		C₂₂H₁₅ClN₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The acylation of 5-(benzyloxy)indole (I) with ethyl chloroformate produced the N-(ethoxycarbonyl)indole (II), which was debenzylated by transfer hydrogenolysis with ammonium formate in the presence of Pd/C to afford the 5-hydroxyindole (III). Condensation of (III) with 3-chloro-4-fluorobenzonitrile (IV) produced the diaryl ether (V). Then, basic hydrolysis of the cyano and ethoxycarbonyl groups of (V) gave the benzoic acid derivative (VI). Finally, N-alkylation of the indole ring of (VI) with 4-phenoxybenzyl bromide (VII) furnished the title compound.

参考文献中间体

合成目标

【1】 Mase, T.; Inami, H.; Hara, H.; Fujii, M; Oritani, H.; Koutoku, H.; Igarashi, S.; A novel class of inhibitors for human steroid 5alpha-reductase: Synthesis and biological evaluation of indole derivatives. II. Chem Pharm Bull 2000, 48, 3, 382.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	30840	5-Benzyloxyindole; benzyl 1H-indol-5-yl ether; 5-(benzyloxy)-1H-indole	1215-59-4	C₁₅H₁₃NO	详情	详情
(II)	51275	ethyl 5-(benzyloxy)-1H-indole-1-carboxylate		C₁₈H₁₇NO₃	详情	详情
(III)	51276	ethyl 5-hydroxy-1H-indole-1-carboxylate		C₁₁H₁₁NO₃	详情	详情
(IV)	51277	3-Chloro-4-fluorobenzonitrile	117482-84-5	C₇H₃ClFN	详情	详情
(V)	51278	ethyl 5-(2-chloro-4-cyanophenoxy)-1H-indole-1-carboxylate		C₁₈H₁₃ClN₂O₃	详情	详情
(VI)	51279	3-chloro-4-(1H-indol-5-yloxy)benzoic acid		C₁₅H₁₀ClNO₃	详情	详情
(VII)	51280	1-(bromomethyl)-4-phenoxybenzene; 4-(bromomethyl)phenyl phenyl ether		C₁₃H₁₁BrO	详情	详情

Extended Information