Phenol → 4-Methyl-3-(2-oxo-3-phenoxy-1(2H)-pyrazinyl)-benzoic acid, methyl ester

HRID 337043

반응식

HRID 337043 반응식
Br[C:2]1[C:3](=[O:20])[N:4]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6](Br)[N:7]=1.[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.C1CC=CCC=1>[Pd].O1CCCC1>[CH3:19][C:18]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[N:4]1[CH:5]=[CH:6][N:7]=[C:2]([O:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]1=[O:20]

참가 물질

7

반응물 4

HCID 996PhenolHCID 123431,4-CyclohexadieneHCID 81531DiisopropylethylamineHCID 66688740methyl 3-(3,5-dibromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate

생성물 1

HCID 866632394-Methyl-3-(2-oxo-3-phenoxy-1(2H)-pyrazinyl)-benzoic acid, methyl ester

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
120 °C

실험 절차

A mixture of 3-(3,5-dibromo-2-oxo-2H-pyrazin-1-yl)-4-methyl-benzoic acid, methyl ester (Example 1b, 400 mg), phenol (400 mg), N,N-diisopropylethylamine (0.4 mL) and tetrahydrofuran (2 mL) was heated within a microwave for 3 h at 120° C. before being cooled to room temperature. The mixture was transferred to a mixture of palladium on carbon (10%, 38 mg) and tetrahydrofuran (1 mL). 1,4-Cyclohexadiene (2 mL) was added and the mixture was heated under atmosphere of nitrogen within a microwave for 15 minutes at 90° C. before being cooled to room temperature. The mixture was filtered and concentrated to give a crude product that was used in the next step without purification.

후처리

  1. temperaturebefore being cooled to room temperature
  2. temperaturethe mixture was heated under atmosphere of nitrogen within a microwave for 15 minutes at 90° C.
  3. temperaturebefore being cooled to room temperature
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-772973e7b197498ab8a77ab4301a1b29
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889692B2

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