Sodium Carbonate → 5-Oxazol-5-yl-pyrazine-2-carboxylic acid

HRID 1409716ノート

反応式

HRID 1409716 の反応式
C([O-])([O-])=O.[Na+].[Na+].C[O:8][C:9]([C:11]1[CH:16]=[N:15][C:14](Cl)=[CH:13][N:12]=1)=[O:10].CC1(C)C(C)(C)OB([C:26]2[O:30][C:29]([Si](C(C)C)(C(C)C)C(C)C)=[N:28][CH:27]=2)O1>CN(C)C=O>[O:30]1[C:26]([C:14]2[N:15]=[CH:16][C:11]([C:9]([OH:8])=[O:10])=[N:12][CH:13]=2)=[CH:27][N:28]=[CH:29]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 442243115-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(tris(propan-2-yl)silyl)-1,3-oxazole

生成物 1

HCID 866861585-Oxazol-5-yl-pyrazine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Aqueous Na2CO3 solution (2 M, 14.5 mL) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium dichloromethane complex (950 mg) are added to a mixture of 5-chloropyrazine-2-carboxylic acid methyl ester (2.00 g) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-[tris(isopropyl)silyl]-oxazole (4.70 g) in N,N-dimethylformamide (20 mL) under an argon atmosphere. The reaction mixture is stirred over night at 80° C. After cooling to room temperature, the solvents are evaporated, the residue is mixed water and acidified with 4 N hydrochloric acid (12 mL). A precipitate is formed upon addition of ethyl acetate, which is filtered off, washed with ethyl acetate and methanol, and dried. LC (method 7): tR=0.46 min; Mass spectrum (ESI−): m/z=190 [M−H]−.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe solvents are evaporated
  3. additionthe residue is mixed water
  4. customA precipitate is formed upon addition of ethyl acetate, which
  5. filtrationis filtered off
  6. washwashed with ethyl acetate and methanol
  7. customdried

出典と根拠

ORDレコード
ord-682feb6dbb594f23b85004f8d104f678
出典データセット
uspto-grants-2014_12
特許番号
US08921398B2

反応ノート

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