Boron Trichloride → HCID 86691629, compound

HRID 624320Notes

Reaction equation

HRID 624320 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([O:25]C(C)C)=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)=[CH:4][CH:3]=1.ClB(Cl)Cl>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([OH:25])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86691628HCID 86691628, compound

Product 1

HCID 86691629HCID 86691629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-yl)-1H-imidazole (800 mg, 2.098 mmol) in dichloromethane (DCM) (80 mL) at −78° C. under an nitrogen atmosphere was added a 1.0 M solution of trichloroborane in DCM (5.24 mL, 5.24 mmol). The reaction mixture was allowed to warm to room temperature and stirring continued at rt overnight. The reaction mixture was then concentrated completely to remove the volatiles. The residue was diluted with ice-cold water, and the solid filtered to obtain the title compound as a yellow solid. Yield: 650 mg (91%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 14.59-15.34 (m, 1H) 11.07 (br s, 1H) 8.35-8.52 (m, 1H) 8.07 (d, J=1.76 Hz, 1H) 7.87-7.99 (m, 1H) 7.59-7.77 (m, 1H) 7.30-7.55 (m, 4H). LCMS: (ES+) m/z=340.15 (M+H)+; Column—ACQUITY UPLC BEH C8 (50×2.1 mm; 1.7 μm); M phase A: 5 mM Ammonium Acetate:MeCN (95:5); M phase B: 5 mM Ammonium Acetate:MeCN (5:95)

Workup

  1. concentrationThe reaction mixture was then concentrated completely
  2. customto remove the volatiles
  3. additionThe residue was diluted with ice-cold water
  4. filtrationthe solid filtered

Sources & evidence

ORD record
ord-fb80b81cb2e84782b6a87888779b3c55
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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