methyl 7-(benzyloxy)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate → HCID 178497265, compound

HRID 2410760Notes

Reaction equation

HRID 2410760 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[CH:19]=[C:18]([C:32]([O:34][CH3:35])=[O:33])[C:14]=3[NH:15][C:16]=2[CH:17]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O.O.C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[CH:19]=[C:18]([C:32]([O:34][CH3:35])=[O:33])[C:14]=3[NH:15][C:16]=2[CH:17]=1

Participants

5

Reactant 1

HCID 66605153methyl 7-(benzyloxy)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate

Product 1

HCID 178497265HCID 178497265, compoundYield 110.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 7-(benzyloxy)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.0 g, 2.1 mmol) in TFA (8.3 mL) and water (2.3 mL) was heated at 90° C. for 3 hrs. The solvent was removed to leave an orange solid. This was suspended in DCM:hexane=1:1 and then collected by filtration to give crude methyl 7-hydroxy-2-(3-(trifluoromethyl)phenyl)-5H-pyrido [3,2-b]indole-4-carboxylate (0.9 g) as a yellow solid that was used as such. MS (ESI) m/z 387.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.49 (1H, s), 8.53 (1H, s), 8.49 (1H, d, J=7.02 Hz), 8.30 (1H, s), 8.11 (1H, d, J=8.24 Hz), 7.75-7.80 (2H, m), 7.13 (1H, d, J=1.83 Hz), 6.81 (1H, dd, J=8.39, 1.98 Hz), 4.07 (3H, s).

Workup

  1. customThe solvent was removed
  2. customto leave an orange solid
  3. filtrationhexane=1:1 and then collected by filtration

Sources & evidence

ORD record
ord-3c3ecb7ba0d74abeb3efd96da51e3400
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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