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【结 构 式】 
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【分子编号】38839 【品名】(3R)-3-[(5-bromo-6-chloro-3-pyridinyl)oxy]-1-pyrrolidinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C10H10BrClN2O3 【 分 子 量 】321.55778 【元素组成】C 37.35% H 3.13% Br 24.85% Cl 11.03% N 8.71% O 14.93% |
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：(IX)The compound has also been obtained by solid phase synthesis. Attachment of (S)-3-hydroxypyrrolidine (VII) to p-nitrophenylcarbonate Wang resin (VI) in the presence of diisopropylethylamine provided the resin bound pyrrolidinol (VIII). Coupling of (VIII) with 3-bromo-2-chloro-5-hydroxypyridine (II) under Mitsunobu conditions gave resin (IX). Further Suzuki coupling of (IX) with 4-cyanophenylboronic acid (IV) afforded (X). The title compound was then cleaved from the resin (X) by treatment with trifluoroacetic acid.
| 【1】 Shank, R.; Davis, C.; Reiltz, A.; Rivero, R.; Lee, J.; Discovery of novel pyridyl ethers as ligand for nicotinic acetylcholine receptor. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 271. |
| 【2】 Davis, C.B.; Shank, R.P.; Reitz, A.B.; Lee, J.; Rivero, R.A.; Synthesis and structure-activity relationship of novel pyridyl ethers for the nicotinic acetylcholine receptor. Bioorg Med Chem Lett 2000, 10, 10, 1063. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 38833 | 5-bromo-6-chloro-3-pyridinol | C5H3BrClNO | 详情 | 详情 | |
| (IV) | 38835 | 4-cyanophenylboronic acid | 126747-14-6 | C7H6BNO2 | 详情 | 详情 |
| (VI) | 38837 | 4-nitrophenyl hydrogen carbonate | C7H5NO5 | 详情 | 详情 | |
| (VII) | 38841 | (3R)-3-pyrrolidinol | C4H9NO | 详情 | 详情 | |
| (VIII) | 38838 | (3R)-3-hydroxy-1-pyrrolidinecarboxylic acid | C5H9NO3 | 详情 | 详情 | |
| (IX) | 38839 | (3R)-3-[(5-bromo-6-chloro-3-pyridinyl)oxy]-1-pyrrolidinecarboxylic acid | C10H10BrClN2O3 | 详情 | 详情 | |
| (X) | 38840 | (3R)-3-[[6-chloro-5-(4-cyanophenyl)-3-pyridinyl]oxy]-1-pyrrolidinecarboxylic acid | C17H14ClN3O3 | 详情 | 详情 |
Extended Information