Boron tribromide → 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylic Acid

HRID 40169Notes

Reaction equation

HRID 40169 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:7]2[C:12]([C:13]=1[C:14](=[O:25])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=1)=[CH:11][CH:10]=[C:9]([O:26][CH3:27])[CH:8]=2)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[F:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[F:23])[CH2:16][NH:15][C:14]([C:13]1[C:12]2[C:7](=[CH:8][C:9]([O:26][CH3:27])=[CH:10][CH:11]=2)[N:6]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:5]=1[C:3]([OH:4])=[O:2])=[O:25]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59762310Methyl 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate2×

Product 1

HCID 597623873-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

General Procedure L. To a solution of methyl3-(3,4-difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate (Compound 93, 149 mg, 0.32 mmol) in CH2Cl2 (10 ml) was added BBr3 (1M in CH2Cl2, 1.6 ml, 1.6 mmol) slowly at 0° C. The mixture was stirred at room temperature for 2 h, and was quenched with ice, extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by PTLC on silica gel (10% MeOH—CH2Cl2) to yield the title compound.

Workup

  1. customwas quenched with ice
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by PTLC on silica gel (10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-d2846b4c27d64b14ae868f0cd481f94a
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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