Trifluoroacetic acid → 2-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515699Notes

Reaction equation

HRID 515699 reaction equation
[CH:1]1([CH2:7][C:8]2[CH:35]=[CH:34][C:11]([CH2:12][O:13][C:14]3[CH:22]=[CH:21][C:20]4[N:19]5[CH2:23][CH2:24][CH:25]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[C:18]5=[CH:17][C:16]=4[CH:15]=3)=[CH:10][C:9]=2[C:36]([F:39])([F:38])[F:37])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(SC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([CH2:7][C:8]2[CH:35]=[CH:34][C:11]([CH2:12][O:13][C:14]3[CH:22]=[CH:21][C:20]4[N:19]5[CH2:23][CH2:24][CH:25]([CH2:26][C:27]([OH:29])=[O:28])[C:18]5=[CH:17][C:16]=4[CH:15]=3)=[CH:10][C:9]=2[C:36]([F:39])([F:37])[F:38])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 67250595tert-Butyl 2-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 583296162-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic AcidYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(7-(4-(cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (50 mg, 0.092 mmol) in DCM (1 mL) was added thioanisole (0.738 mmol) and TFA (1.85 mmol). The reaction mixture was stirred for 3 h. The solvent was removed under vacuum. The residue was purified by preparative HPLC/MS to give the title compound as a solid (26.1 mg). LCMS m/z=486.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90-1.04 (m, 2H), 1.08-1.20 (m, 3H), 1.54-1.70 (m, 6H), 2.15-2.26 (m, 1H), 2.55 (dd, J=16.29, 8.08 Hz, 1H), 2.62 (d, J=6.44 Hz, 2H), 2.65-2.72 (m, 1H), 2.72-2.83 (m, 1H), 3.52-3.63 (m, 1H), 3.91-4.01 (m, 1H), 4.05-4.14 (m, 1H), 5.12 (s, 2H), 6.01 (s, 1H), 6.77 (dd, J=8.72, 2.40 Hz, 1H), 7.07 (d, J=2.40 Hz, 1H), 7.19 (d, J=8.59 Hz, 1H), 7.44 (d, J=8.08 Hz, 1H), 7.66 (d, J=7.71 Hz, 1H), 7.74 (s, 1H), 12.27 (bs, 1H).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was purified by preparative HPLC/MS

Sources & evidence

ORD record
ord-950d3501c2aa413c837144e472a3bd57
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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