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

HRID 68771

反応式

HRID 68771 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-d82ac1979eda48fe8aed6529bddb05a5
出典データセット
uspto-grants-2014_09
特許番号
US08822471B2

関連ノート

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