Imidazole → HCID 67452891, compound

HRID 1519226Notes

Reaction equation

HRID 1519226 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21]O)=[N:6][CH:7]=1.N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:48]>C(Cl)Cl.O>[Br:48][CH2:21][C:10]1[N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:13][C:9]=1[S:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 71184222HCID 71184222, compound2×

Product 1

HCID 67452891HCID 67452891, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol (intermediate B1.1, 0.30 g, 0.89 mmol) in 3.3 mL of DCM at 0° C. was added imidazole (0.02 g, 0.36 mmol), Ph3P (0.28 g, 1.07 mmol) and CBr4 (0.36 g, 1.07 mmol). After 1 h at 0° C., water was added and the reaction mixture was extracted with EtOAc. The combined organics were washed with 10% KHSO4, satd. NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The reaction was purified by flash chromatography (silica, 0-25% EtOAc/hexanes) to give 2-{[4-(bromomethyl)-2-(4-fluorophenyl)-1,3-oxazol-5-yl]sulfanyl}-5-chloropyridine as white solid. LCMS [M+H]+=401.2.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washThe combined organics were washed with 10% KHSO4
  3. dry with materialNaHCO3 and brine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe reaction was purified by flash chromatography (silica, 0-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4f0d106e3606462bbbe7f4e5bc330bce
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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