Sodium Carbonate → 3-Fluoro-4-oxazol-5-yl-benzoic acid

HRID 68771

반응식

HRID 68771 반응식
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].CC1(C)C(C)(C)OB([C:20]2[O:24][C:23]([Si](C(C)C)(C(C)C)C(C)C)=[N:22][CH:21]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.Cl[Pd]Cl>[F:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[C:20]1[O:24][CH:23]=[N:22][CH:21]=1)[C:6]([OH:8])=[O:7]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27733414-Bromo-3-fluorobenzoic acidHCID 442243115-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(tris(propan-2-yl)silyl)-1,3-oxazole

생성물 1

HCID 682901443-Fluoro-4-oxazol-5-yl-benzoic acid

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-bromo-3-fluoro-benzoic acid (1.00 g), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-triisopropylsilanyl-oxazole (1.90 g), PdCl2 [1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (400 mg), and aqueous Na2CO3 solution (2 M; 5.70 mL) in N,N-dimethylformamide (6 mL) is stirred overnight at 80° C. under an argon atmosphere. After cooling to room temperature the reaction mixture is concentrated in vacuo and water is added. The resulting mixture is acidified with hydrochloric acid (4 M; 6 mL) and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is triturated with diethyl ether, filtered off and dried to give the title product. LC (method 1): tR=0.87 min; Mass spectrum (ESI+): m/z=208 [M+H]+.

후처리

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. concentrationis concentrated in vacuo and water
  3. additionis added
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts are washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue is triturated with diethyl ether
  9. filtrationfiltered off
  10. customdried

출처 및 근거

ORD 기록
ord-d82ac1979eda48fe8aed6529bddb05a5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822471B2

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