Trifluoroacetic acid methylene chloride → 5-(Benzyloxy)-1-(phenylsulfonyl)-4-(piperazin-1-ylmethyl)-1H-indole

HRID 1159812Notes

Reaction equation

HRID 1159812 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:27][N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.ClCCl>>[CH2:1]([O:8][C:9]1[C:10]([CH2:27][N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86618249tert-Butyl 4-{[5-(benzyloxy)-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1-carboxylate2×

Product 1

HCID 595135815-(Benzyloxy)-1-(phenylsulfonyl)-4-(piperazin-1-ylmethyl)-1H-indoleYield 41.2%

Procedure

tert-Butyl 4-{[5-(benzyloxy)-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1-carboxylate (30 mg, 0.05 mmol, Intermediate 63) was stirred with a 50/50 mixture of TFA/dichlorometane (3 mL) in room temperature for four hours. The solvent was removed at reduced pressure and the crude was purified on a preparative HPLC, method B, to give 9.5 mg (40%) of a colorless oil. MS (ESI+) for C26H27N3O3S m/z 462 (M+H)+.

Workup

  1. customThe solvent was removed at reduced pressure
  2. customthe crude was purified on a preparative HPLC, method B

Sources & evidence

ORD record
ord-37c915aaeae44d25b0ca1823fea4a148
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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