Sodium Carbonate → Methyl 3-amino-6-(4-(methylsulfonyl)phenyl)pyrazine-2-carboxylate

HRID 78559

반응식

HRID 78559 반응식
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([C:20]2[CH:21]=[CH:22][C:17]([S:14]([CH3:13])(=[O:16])=[O:15])=[CH:18][CH:19]=2)=[CH:6][N:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 27343644-(Methanesulfonyl)phenylboronic acid

생성물 1

HCID 51000410Methyl 3-amino-6-(4-(methylsulfonyl)phenyl)pyrazine-2-carboxylate수율 53%

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (1.5 g, 6.465 mmol), (4-methylsulfonylphenyl)boronic acid (1.552 g, 7.758 mmol), bis(triphenylphosphine) palladium(II)dichloride (226.9 mg, 0.3233 mmol), and Na2CO3 (9.700 mL of 2 M, 19.40 mmol) in DME (18.75 mL) were heated in the microwave at 110° C. for 1 hour. The resultant mixture was diluted with EtOAc and washed with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (50% EtOAc/hexanes) to afford the title compound (600 mg, 53% Yield).

후처리

  1. washwashed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel by flash column chromatography (50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c79dc17f14994985b8414819b5254db4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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