Boron tribromide → HCID 136499144, compound

HRID 1524035Notes

Reaction equation

HRID 1524035 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[O:25]C)[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.B(Br)(Br)Br.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>ClCCl>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([C:7]2[CH:6]=[CH:5][C:4]([C:15]3[C:16]([OH:25])=[CH:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=3)=[CH:3][C:2]=2[F:1])=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 90313982HCID 90313982, compound

Product 1

HCID 136499144HCID 136499144, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-[3-fluoro-2′-methoxy-4′-(trifluoromethyl)biphenyl-4-yl]pyrazin-2-amine (370 mg, 1.02 mmol) in dry dichloromethane (9.8 mL) at −78° Celsius, was added a boron tribromide in dichloromethane (3.1 mL, 1 M). The flask was slowly warmed to rt and stirred overnight. The reaction was poured into sat. NH4Cl and the pH adjusted to 8 with saturated NaHCO3. The resultant mixture was extracted with DCM (3×30 mL) and the combined extracts dried over Na2SO4, filtered and concentrated to dryness. The crude product was purified by HPLC to give the title compound. MS (ESI): mass calcd. for C17H11F4N3O, 349.08; m/z found, 350.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.41-8.35 (m, 1H), 8.17-8.10 (d, J=1.5, 1H), 7.99-7.88 (m, 1H), 7.56-7.46 (m, 3H), 7.22-7.19 (m, 1H), 7.19-7.17 (d, J=1.7, 1H).

Workup

  1. extractionThe resultant mixture was extracted with DCM (3×30 mL)
  2. dry with materialthe combined extracts dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-d3bde42b02664500a5710c03700e4035
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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