Boron tribromide → Ammonia

HRID 500627Notes

Reaction equation

HRID 500627 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:38]([O:39]C)=[CH:37][CH:36]=[CH:35][C:7]=1[O:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([CH3:34])([CH3:33])[CH2:15][CH2:16][C:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([NH2:20])=[O:19])[CH2:10]1>ClCCl>[NH3:11].[F:5][C:6]1[C:38]([OH:39])=[CH:37][CH:36]=[CH:35][C:7]=1[O:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([CH3:34])([CH3:33])[CH2:15][CH2:16][C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:18]([NH2:20])=[O:19])[CH2:10]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 59423948HCID 59423948, compound

Product 2

HCID 222AmmoniaHCID 16065266HCID 16065266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M in dichloromethane, 1.1 mL, 1.224 mmol) was added to an ice-cooled solution of the product of example 75 (140 mg, 0.286 mmol) in dichloromethane (4 mL) and the mixture was stirred at room temperature for 2 hours. The reaction was quenched with 0.88 ammonia solution and stirred at room temperature for 16 hours. The reaction mixture was adjusted to pH 8 by dropwise addition of 2N hydrochloric acid (aq) and extracted with dichloromethane (2×10 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 yellow foam in 15% yield, 20 mg.

Workup

  1. customThe reaction was quenched with 0.88 ammonia solution
  2. stirringstirred at room temperature for 16 hours
  3. additionThe reaction mixture was adjusted to pH 8 by dropwise addition of 2N hydrochloric acid (aq)
  4. extractionextracted with dichloromethane (2×10 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-124df441cbdd43e0866717c16516d0f4
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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