Water → HCID 86587389, compound

HRID 1357271Notes

Reaction equation

HRID 1357271 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[C:15]([O:16]C)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH2:18][N:19]([CH3:36])[C:20]([C:22]1[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[C:23]=1[CH2:32][CH2:33][CH2:34][CH3:35])=[O:21])=[CH:11]2.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[Br:5][C:6]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH2:18][N:19]([CH3:36])[C:20]([C:22]1[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[C:23]=1[CH2:32][CH2:33][CH2:34][CH3:35])=[O:21])=[CH:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 18522661Acetone cardice2×HCID 86587390HCID 86587390, compound

Product 1

HCID 86587389HCID 86587389, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Boron tribromide (18.78 mL of a 1 M solutioin in methylene chloride; 18.78 mmol) in 20 mL of methylene chloride was added under nitrogen dropwise over fifteen minutes to a solution of 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide (3.09 g, 6.26 mmol), prepared in the previous step, in 125 mL of methylene chloride at dry ice-acetone temperature. After the addition the dry ice-acetone bath was replaced with an ice bath and the stirring continued for 4 h. Water was added to the reaction at ice bath temperature. The organic layer was separated and the aqueous layer extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (3.22 g, 100%) as a brown solid foam, MS m/z: 479 [M+H]+.

Workup

  1. customwas replaced with an ice bath
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted three times with methylene chloride
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1acbc25015f04ebabbdc6782d775452b
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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