Boron tribromide → Ammonia

HRID 2387684Notes

Reaction equation

HRID 2387684 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([O:39]C)[CH:38]=1)[O:9][C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]([CH3:35])([CH3:34])[CH2:16][CH2:17][C:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([NH2:21])=[O:20])[CH2:11]1>ClCCl>[NH3:12].[F:5][C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([OH:39])[CH:38]=1)[O:9][C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]([CH3:34])([CH3:35])[CH2:16][CH2:17][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:19]([NH2:21])=[O:20])[CH2:11]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 59423935HCID 59423935, compound

Product 2

HCID 222AmmoniaHCID 54757544HCID 54757544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M in dichloromethane, 1.2 mL, 1.224 mmol) was added to an ice-cooled solution of the product of example 73 (150 mg, 0.306 mmol) in dichloromethane (4 mL) and the mixture was stirred at room temperature for 18 hours. The reaction was quenched with 0.88 ammonia solution and stirred at room temperature for 2 hours. The reaction mixture was adjusted to pH 8 by dropwise addition of 2N hydrochloric acid (aq) and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 95:5:0.5, afforded the title compound as a pale brown foam in 49% yield, 71 mg.

Workup

  1. customThe reaction was quenched with 0.88 ammonia solution
  2. stirringstirred at room temperature for 2 hours
  3. additionThe reaction mixture was adjusted to pH 8 by dropwise addition of 2N hydrochloric acid (aq)
  4. extractionextracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by column chromatography on silica gel
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-48e10668dfe944c2a9eaf32c16df6449
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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