Boron tribromide → HCID 15951892, compound

HRID 2244232Notes

Reaction equation

HRID 2244232 reaction equation
C([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:12][CH:11]=1)C.B(Br)(Br)Br>ClCCl>[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15951891HCID 15951891, compound

Product 1

HCID 15951892HCID 15951892, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 10-[(2′-ethoxy-1,1′-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 33 (0.281 g, 0.518 mmol) in dry dichloromethane (2.6 mL) at 0° C. under nitrogen was added dropwise a 1.0 M solution of boron tribromide in dichloromethane (2.6 mL, 2.6 mmol) over ca. 5 minutes. The reaction mixture was allowed to warm to room temperature and then stirred for 5 hours. The reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a tan solid (0.210 g). Purification by flash chromatography using a solvent gradient of 1 to 4% methanol in dichloromethane gave the title compound (0.042 g, 16%) as a white solid.

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (50 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc383d1cb44b418db1605df28ffbb065
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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