7-[(Methylsulfanyl)methyl]-1H-indole → 3-[1-Cyclopropyl-1-(2,2-difluoro-1,3-benzodioxol-5-yl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561640Notes

Reaction equation

HRID 561640 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.[CH:13]1([C:16]([C:19]2[CH:29]=[CH:28][C:22]3[O:23][C:24]([F:27])([F:26])[O:25][C:21]=3[CH:20]=2)(O)[CH3:17])[CH2:15][CH2:14]1.C1(C(C2C3C(=C(CSC)C=CC=3)NC=2)(C2C=CC(OC)=C(F)C=2)C)CC1>>[CH:13]1([C:16]([C:9]2[C:8]3[C:12](=[C:4]([CH2:3][S:2][CH3:1])[CH:5]=[CH:6][CH:7]=3)[NH:11][CH:10]=2)([C:19]2[CH:29]=[CH:28][C:22]3[O:23][C:24]([F:26])([F:27])[O:25][C:21]=3[CH:20]=2)[CH3:17])[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 583923303-[1-Cyclopropyl-1-(3-fluoro-4-methoxyphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583925051-Cyclopropyl-1-(2,2-difluoro-1,3-benzodioxol-5-yl)ethanol

Product 1

HCID 583922173-[1-Cyclopropyl-1-(2,2-difluoro-1,3-benzodioxol-5-yl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Procedure

The title compound was prepared starting from 32 mg (0.18 mmol) of the compound from Example 8A and 43 mg (0.18 mmol) of the compound from Example 144A in analogy to the synthesis of the compound from Example 186. 38 mg (53% of theory) of the target compound were obtained.

Workup

  1. custom38 mg (53% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-797e3b9332814d2ab138c8f12ca642d9
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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