Boron tribromide → HCID 51356770, compound

HRID 389994Notes

Reaction equation

HRID 389994 reaction equation
B(Br)(Br)Br.[CH2:5]([C:7]1[C:33]([F:34])=[CH:32][C:10]([O:11][C:12]2[CH:30]=[CH:29][C:15]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH2:27])=[O:26])[C:20](=[O:28])[CH2:19]3)=[O:17])=[CH:14][C:13]=2[F:31])=[C:9]([O:35]C)[CH:8]=1)[CH3:6].[Cl-].[NH4+]>ClCCl>[CH2:5]([C:7]1[C:33]([F:34])=[CH:32][C:10]([O:11][C:12]2[CH:30]=[CH:29][C:15]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH2:27])=[O:26])[C:20](=[O:28])[CH2:19]3)=[O:17])=[CH:14][C:13]=2[F:31])=[C:9]([OH:35])[CH:8]=1)[CH3:6]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 67116145HCID 67116145, compound

Product 1

HCID 51356770HCID 51356770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A commercial solution of boron tribromide (1N in DCM, 0.84 mL, 0.84 mmol) was added to a solution of 2-[4-(4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]-2-oxopiperazin-1-yl)acetamide (which may be prepared in accordance with the experimental described in Example 6, step 1; 140 mg, 0.31 mmol) in dichloromethane (1 mL) placed under argon at −30° C. The reaction mixture was stirred at room temperature overnight and diluted by addition of dichloromethane (20 mL) and a saturated solution of ammonium chloride (20 mL). After separation, the aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (95:5 to 90:10) as eluent. The title product was obtained as a white solid (30 mg, 22%).

Workup

  1. custommay be prepared in accordance with the
  2. customplaced under argon at −30° C
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-74b534a1675c4a2aae670a692ef6b166
Source dataset
uspto-grants-2013_02
Patent number
US08383621B2

Reaction notes

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