Boron tribromide → HCID 16038473, compound

HRID 639211Notes

Reaction equation

HRID 639211 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24]([NH:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=4)=[O:25])=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:42].B(Br)(Br)Br>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24]([NH:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=4)=[O:25])=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:42]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 16038472HCID 16038472, compound

Product 1

HCID 16038473HCID 16038473, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10-[(2,2′-dimethyl-1,1′-biphenyl-4-yl)carbonyl]-N-(4-methoxybenzyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 8 (243 mg, 0.437 mmol) in dichloromethane (1.5 mL) at 0° C. under nitrogen was added a solution of boron tribromide in dichloromethane (1.0 M, 1.5 mL, 1.5 mmol) dropwise over 5 minutes. After 10 minutes at 0° C. the cooling bath was removed and the solution allowed to warm slowly to room temperature over 1.5 hours. The reaction was quenched by the addition of saturated aqueous sodium hydrogen carbonate solution (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with a saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a reddish oil (305 mg). Purification by flash chromatography using a solvent gradient of 0 to 2% methanol in dichloromethane gave the title compound (119 mg, 52%) as a white solid. MS [(+)ESI, m/z]: 542 [M+H]+.HRMS [(+)ESI, m/z]: 542.24405. Calcd for C35H32N3O3: 542.24437. Anal. Calcd for C35H31N3O3: C, 77.61; H, 5.77; N, 7.76. Found: C, 77.54; H, 5.79; N, 7.72.

Workup

  1. customAfter 10 minutes at 0° C. the cooling bath was removed
  2. customThe reaction was quenched by the addition of saturated aqueous sodium hydrogen carbonate solution (20 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washThe combined organic extracts were washed with a saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57f6d743a78f4a1697c16119e135f50e
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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