Water → [(S)-4-(3-Allyloxy-pyridin-2-ylmethyl)-7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-carbamic acid isopropyl ester

HRID 449849Notes

Reaction equation

[CH:1]([O:4][C:5](=[O:21])[NH:6][C@@H:7]1[CH2:20][C:10]2[NH:11][C:12]3[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][C:17]=3[C:9]=2[CH2:8]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28]([O:31][C:32]1[C:33]([CH2:38]Cl)=[N:34][CH:35]=[CH:36][CH:37]=1)[CH:29]=[CH2:30].O>CN(C)C=O>[CH:1]([O:4][C:5](=[O:21])[NH:6][C@@H:7]1[CH2:20][C:10]2[N:11]([CH2:38][C:33]3[C:32]([O:31][CH2:28][CH:29]=[CH2:30])=[CH:37][CH:36]=[CH:35][N:34]=3)[C:12]3[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][C:17]=3[C:9]=2[CH2:8]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

((S)-7-Cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid isopropyl ester (25 g, 88.2 mmol) is dissolved in dimethylformamide (150 mL) under nitrogen. Cesium carbonate (57.5 g, 176.5 mmol) and 3-allyloxy-2-chloromethyl-pyridine (16.2 g, 88.2 mmol) are added sequentially. The reaction mixture is stirred at 40° C. for 16 h. The reaction is cooled to room temperature and added to water (1250 mL). After one hour of stirring a pale cream solid is filtered. The crude material is purified by recrystallization from i-PrOH and then dried under vacuum to constant weight to afford the title compound (32 g; 84%). LC-ES/MS m/z: 431.2 [M+H]+.

Workup

temperatureThe reaction is cooled to room temperature
stirringAfter one hour of stirring a pale cream solid
filtrationis filtered
customThe crude material is purified by recrystallization from i-PrOH
customdried under vacuum to constant weight

Sources & evidence

ORD record: ord-e4301afa600e424b92fa2f3dd39622a4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486943B2

Reaction notes

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