Trifluoroacetic acid → phenyl 2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl sulfide trifluoroacetate

HRID 1356272Notes

Reaction equation

HRID 1356272 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3[CH2:19][CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22][CH2:23][C:11]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH2:19]1[C:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[N:10]([CH2:9][CH2:8][S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]=2[CH2:23][CH2:22][NH:21][CH2:20]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22396645tert-butyl 6-[2-(phenylsulfanyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Product 1

HCID 22396874phenyl 2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl sulfide trifluoroacetate

Procedure

tert-Butyl 6-[2-(phenylsulfanyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0532 g, 0126 mmol) was dissolved in trifluoroacetic acid (2 mL), and the solution was stirred for 5 min. The reaction mixture was concentrated to dryness to give phenyl 2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl sulfide trifluoroacetate (0.70 g) as a tan solid. 1H NMR (300 MHz, CD3OD) δ 3.12, 3.18, 3.30, 3.34-3.41, 4.41, 7.08, 7.15, 7.17-7.26, 7.45; MS (ESI+) for C20H22N2S m/z 323.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-93118da361214fd596b35c0ade1a7429
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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