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

HRID 1409716노트

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HRID 1409716 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-682feb6dbb594f23b85004f8d104f678
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921398B2

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