Trifluoroacetic acid → 3-[1-Cyclopropyl-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561638Notes

Reaction equation

HRID 561638 reaction equation
[CH:1]1([C:4]([C:7]2[CH:16]=[CH:15][C:10]3[O:11][CH2:12][CH2:13][O:14][C:9]=3[CH:8]=2)(O)[CH3:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:24][S:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:35]=1[NH:34][CH:33]=[CH:32]2>ClCCl>[CH:1]1([C:4]([C:32]2[C:31]3[C:35](=[C:27]([CH2:26][S:25][CH3:24])[CH:28]=[CH:29][CH:30]=3)[NH:34][CH:33]=2)([C:7]2[CH:16]=[CH:15][C:10]3[O:11][CH2:12][CH2:13][O:14][C:9]=3[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 58392439alpha-Cyclopropyl-2,3-dihydro-alpha-methyl-1,4-benZodioxin-6-methanol

Product 1

HCID 445953853-[1-Cyclopropyl-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg (1.82 mmol) of the compound from Example 142A and 0.17 ml (2.18 mmol) of trifluoroacetic acid were added to 322 mg (1.82 mmol) of the compound from Example 8A in 3 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min, and the crude product was then purified twice by preparative HPLC (mobile phase: acetonitrile/water gradient) and by recrystallization from acetonitrile. 184 mg (27% of theory) of the title compound were obtained.

Workup

  1. customthe crude product was then purified twice by preparative HPLC (mobile phase: acetonitrile/water gradient) and by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-909aea943d0c46ecbdb73445f790f4d0
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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