Trifluoroacetic acid → HCID 58329587, compound

HRID 1964112Notes

Reaction equation

HRID 1964112 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:33]=[CH:32][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:16]5=[CH:15][C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:34]([F:37])([F:36])[F:35])[CH2:3][CH2:2]1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([CH2:4][O:5][C:6]2[CH:33]=[CH:32][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([OH:27])=[O:26])[C:16]5=[CH:15][C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:34]([F:37])([F:35])[F:36])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 67250575HCID 67250575, compound

Product 1

HCID 58329587HCID 58329587, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(7-(4-(cyclopropylmethoxy)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (48.4 mg, 0.094 mmol) in DCM (1 mL) was added anisole (0.110 mL, 0.939 mmol) and TFA (0.209 mL, 2.82 mmol). The reaction mixture was stirred for 1 hour. The solvent was removed under vacuum. The residue was purified by preparative HPLC/MS to give the title compound as a solid (3.8 mg). LCMS m/z=460.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.29-0.38 (m, 2H), 0.50-0.61 (m, 2H), 1.14-1.28 (m, 1H), 2.14-2.26 (m, 1H), 2.53-2.61 (m, 1H), 2.63-2.72 (m, 1H), 2.72-2.83 (m, 1H), 3.52-3.61 (m, 1H), 3.89-4.03 (m, 3H), 4.04-4.16 (m, 1H), 5.06 (s, 2H), 6.01 (s, 1H), 6.75 (dd, J=8.72, 2.40 Hz, 1H), 7.06 (d, J=2.27 Hz, 1H), 7.18 (d, J=8.59 Hz, 1H), 7.24 (d, J=8.08 Hz, 1H), 7.61-7.72 (m, 2H), 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-8a3d639b6dc647e680f1870faf9a6fc6
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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