Phosphorus tribromide → HCID 69673085, compound

HRID 2283250Notes

Reaction equation

HRID 2283250 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]=2[C:13]2[O:14][CH:15]=[C:16]([CH2:18]O)[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:27]>C(Cl)Cl>[Br:27][CH2:18][C:16]1[N:17]=[C:13]([C:12]2[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:10][N:9]=[N:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:14][CH:15]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 69673993HCID 69673993, compound

Product 1

HCID 69673085HCID 69673085, compoundYield 193.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(3,5-diphenylpyridazin-4-yl)oxazol-4-yl)methanol (220 mg, 0.66 mmol) in DCM (8 mL), PBr3 (91 mg, 0.33 mmol) was added at 0° C. and the reaction mixture was warmed to rt and stirred for 12 h. After completion of starting material, reaction was quenched with saturated NaHCO3 solution, extracted with ethyl acetate (2×25 mL), washed with brine (1×10 mL). Solvent was removed under reduced pressure to obtain the crude product 4-(bromomethyl)-2-(3,5-diphenylpyridazin-4-yl)oxazole (250 mg) which was carried to next step without further purification.

Workup

  1. customAfter completion of starting material, reaction
  2. customwas quenched with saturated NaHCO3 solution
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. washwashed with brine (1×10 mL)
  5. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-54db74b0857045fb99124e13d221b1f9
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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