Boron tribromide → HCID 66900210, compound

HRID 1918189Notes

Reaction equation

HRID 1918189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[C:14]([C:23]([F:26])([F:25])[F:24])[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:27]C.B(Br)(Br)Br>C(Cl)Cl>[C:2]1([N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([OH:27])[CH:4]=2)[C:9]([NH:11][C:12]2[N:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:15]=[C:14]([C:23]([F:25])([F:24])[F:26])[CH:13]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66875933HCID 66875933, compound

Product 1

HCID 66900210HCID 66900210, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-fluoro-3-methoxyphenyl)-3-(1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)urea (0.985 g, 2.5 mmol) in DCM (30 mL) at ice-water bath was dropped a 1.0 M solution of BBr3 in DCM (25 mL) and it was stirred for 2 hours. The reaction mixture was quenched with saturated NaHCO3 solution and extracted with DCM. Extracts were dried over MgSO4 and concentrated. The crude product was purified on a silica gel column using a mixture of EtOAc-hexane as eluent to give phenyl 1-(4-fluoro-3-hydroxyphenyl)-3-(1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)urea as solid (0.327 g, 34%). 1H NMR (300 MHz, DMSO-d6) 6.59 (s, 1H), 6.65 (d, 1H), 6.78 (dd, 1H), 7.34 (m, 2H), 7.49 (m, 2H), 7.57 (d, 1H), 7.65 (d, 1H), 8.54 (s, 1H), 8.94 (s, 1H), 10.00 (s, 1H); LC-MS (ESI) m/z 381 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with DCM
  3. dry with materialExtracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column
  6. additiona mixture of EtOAc-hexane as eluent

Sources & evidence

ORD record
ord-dc084604d50a48c790823816108fa5bf
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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