Boron tribromide → HCID 57656314, compound

HRID 2041130Notes

Reaction equation

HRID 2041130 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:14])([F:13])[F:15])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57656015HCID 57656015, compound

Product 1

HCID 57656314HCID 57656314, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 7-chloro-6-(4-methoxybenzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.667 g) in DCM (40 mL). Add a 1M solution of boron tribromide in DCM (10 mL) at 0° C. Stir the reaction for 12 h and gradually raise to room temperature. Quench the reaction with saturated aqueous NaHCO3 and extract with DCM three times. Combine the organic extracts, wash with brine, dry over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:3) to give the title compound as an oil (888 mg). MS (ES+) m/z: 399 (M+1)+.

Workup

  1. customthe reaction for 12 h
  2. customQuench
  3. customthe reaction with saturated aqueous NaHCO3
  4. extractionextract with DCM three times
  5. washCombine the organic extracts, wash with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:3)

Sources & evidence

ORD record
ord-0767f7330f1f4a98b5e8dae8b261fe95
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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