Boron tribromide → HCID 57656314, compound

HRID 911242Notes

Reaction equation

HRID 911242 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-f728b70cd9404527808abeebf913c688
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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