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【结 构 式】

【分子编号】44819

【品名】furo[2,3-b]pyridine-2-carbaldehyde

【CA登记号】

【 分 子 式 】C8H5NO2

【 分 子 量 】147.13324

【元素组成】C 65.31% H 3.43% N 9.52% O 21.75%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

Oxidation of aldehyde (I) with AgNO3 in EtOH/H2O in the presence of KOH provides carboxylic acid (II), which is then converted into acid chloride (III) by means of (COCl)2 in CH2Cl2 and catalytic DMF. Treatment of (III) with trimethylsilyl diazomethane (TMSCH2N2) in Et2O followed by HCl(g) in Et2O furnishes chloro derivative (IV), which is then enantioselectively reduced by means of (-)-Dip-Cl to afford alcohol (V). Treatment of (V) with NaOH in THF/H2O induces formation of epoxy derivative (VI), which is then condensed with amine (VII) to yield compound (VIII). N-Protection of (VIII) by reaction with Boc2O in CH2Cl2, followed by reduction of the nitro moiety by hydrogenation over Pd(OH)2 in MeOH, gives amine (IX). Amine (IX) is converted into sulfonamide (XI) by reaction with sulfonyl chloride (X) in CH2Cl2 in the presence of pyridine. Finally, the Boc group of (XI) is removed by means of TFA in CH2Cl2 to furnish the desired product.

1 Lambert, M.H.; Xu, H.E.; Collins, J.L.; Willson, T.M.; Henke, B.R.; Oplinger, J.A.; Brown, P.J.; PPAR agonists for metabolic diseases. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 197.
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) 44819 furo[2,3-b]pyridine-2-carbaldehyde C8H5NO2 详情 详情
(II) 44820 furo[2,3-b]pyridine-2-carboxylic acid C8H5NO3 详情 详情
(III) 44821 furo[2,3-b]pyridine-2-carbonyl chloride C8H4ClNO2 详情 详情
(IV) 44822 2-chloro-1-furo[2,3-b]pyridin-2-yl-1-ethanone C9H6ClNO2 详情 详情
(V) 44823 (1R)-2-chloro-1-furo[2,3-b]pyridin-2-yl-1-ethanol C9H8ClNO2 详情 详情
(VI) 44824 2-[(2S)oxiranyl]furo[2,3-b]pyridine C9H7NO2 详情 详情
(VII) 26560 4-nitrophenethylamine 24954-67-4 C8H10N2O2 详情 详情
(VIII) 44825 (1S)-1-furo[2,3-b]pyridin-2-yl-2-[(4-nitrophenethyl)amino]-1-ethanol C17H17N3O4 详情 详情
(IX) 44826 tert-butyl 4-aminophenethyl[(2S)-2-furo[2,3-b]pyridin-2-yl-2-hydroxyethyl]carbamate C22H27N3O4 详情 详情
(X) 44827 4-[4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonyl chloride C16H9ClF3NO2S2 详情 详情
(XI) 44828 tert-butyl (2S)-2-furo[2,3-b]pyridin-2-yl-2-hydroxyethyl(4-[[(4-[4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]phenyl)sulfonyl]amino]phenethyl)carbamate C38H35F3N4O6S2 详情 详情
Extended Information