Boron tribromide → Ammonia

HRID 2387685Notes

Reaction equation

HRID 2387685 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, 10.1 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-b7c03e2fd5af4e60a082773c3affe5ec
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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