Cesium carbonate → (S)-isopropyl 7-cyano-4-(3-fluoro-2-methoxybenzyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate

HRID 449834Notes

Reaction equation

HRID 449834 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].Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=1[O:31][CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[CH:1]([O:4][C:5](=[O:21])[NH:6][C@@H:7]1[CH2:20][C:10]2[N:11]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=3[O:31][CH3:32])[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

6

Reactant 3

HCID 10796Cesium carbonateHCID 225059631-(Chloromethyl)-3-fluoro-2-methoxybenzeneHCID 66933207(S)-(7-Cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamic Acid Isopropyl Ester

Product 1

HCID 66933184(S)-isopropyl 7-cyano-4-(3-fluoro-2-methoxybenzyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester (1.50 g, 5.29 mmol) and 1-(chloromethyl)-3-fluoro-2-methoxybenzene (1.11 g, 6.35 mmol) in N,N-dimethylformamide (10 mL) is treated with cesium carbonate (2.59 g, 7.94 mmol) at room temperature and stirred overnight under nitrogen. The reaction mixture is diluted with water and ether/hexanes. The white solids that crash out of solution are filtered, rinsed with water, ether, hexanes, and dried under vacuum at 50° C. for 48 h to obtain the title compound as a white solid (2.18 g, 98%). LC-ES/MS m/z 422.2 [M+H]+, TR=4.57 min.

Workup

  1. filtrationThe white solids that crash out of solution are filtered
  2. washrinsed with water, ether, hexanes
  3. customdried under vacuum at 50° C. for 48 h

Sources & evidence

ORD record
ord-14f2b7c6224d4eaba733278a11bffaa0
Source dataset
uspto-grants-2013_07
Patent number
US08486943B2

Reaction notes

Loading…