Water → HCID 68859841, compound

HRID 493493Notes

Reaction equation

HRID 493493 reaction equation
B(Br)(Br)Br.[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]([N:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([O:38]C)=[C:34]([Br:40])[CH:33]=3)=[CH:28][CH:27]=2)[CH3:24])=[O:22])=[CH:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]([N:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([Br:40])[CH:33]=3)=[CH:28][CH:27]=2)[CH3:24])=[O:22])=[CH:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 18522661Acetone cardice2×HCID 68860394HCID 68860394, compound

Product 1

HCID 68859841HCID 68859841, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (41.4 mL of a 1 M solution in methylene chloride; 41.4 mmol) was added under nitrogen dropwise over 30 minutes to a solution of 1-benzyl-N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-N-methyl-1H-indole-3-carboxamide (7.46 g, 13.8 mmol), prepared in the previous step, in 200 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 was continued for 3.5 h. At ice bath temperature 50 mL of water was added dropwise. The reaction was then partitioned between additional amounts of methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 1-benzyl-N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-N-methyl-1H-indole-3-carboxamide (7.13 g, 98%) as a light tan solid, mp 164-170° C. Elemental Analysis for C30H25BrN2O2 Calc'd: C, 68.58; H, 4.80; N, 5.33. Found: C, 67.27; H, 4.78; N, 5.19

Workup

  1. customwas replaced with an ice bath
  2. customThe reaction was then partitioned between additional amounts of methylene chloride and water
  3. customThe aqueous layer was separated
  4. extractionextracted three times with methylene chloride
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b87dee52b2b841bda2daa9ef35275d9f
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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