(2s)-Glycidyl indol-4-yl ether → HCID 70217223, compound

HRID 1900996Notes

Reaction equation

HRID 1900996 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:23]=[C:22]([C:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH:29]=3)[S:21][C:20]=2[CH:30]=1>C(O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:23]=[C:22]([C:24]3[CH2:25][CH2:26][N:27]([CH2:3][C@H:2]([OH:1])[CH2:4][O:5][C:6]4[CH:14]=[CH:13][CH:12]=[C:11]5[C:7]=4[CH:8]=[CH:9][NH:10]5)[CH2:28][CH:29]=3)[S:21][C:20]=2[CH:30]=1

Participants

4

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 21268229HCID 21268229, compound

Product 1

HCID 70217223HCID 70217223, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 1 using (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.166 g, 0.088 mmol) and 6-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)benzo[b]thiophene (0.200 g, 0.080 mmol) using ethanol as reaction solvent. Yield 0.122 g (35%) of a tan powder. FDMS m/e=438 (M+ of free base).

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-9ac6dd7597e0467dbd5292ffb35c303d
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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