Sodium Carbonate → Methyl 3-methoxy-6-methylpyrazine-2-carboxylate

HRID 914836노트

반응식

HRID 914836 반응식
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:13])=[N:4][CH:3]=1.[CH3:14][Zn]C.[Cl-].[NH4+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:13][O:12][C:5]1[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]([CH3:14])=[CH:3][N:4]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 22248028Methyl 6-bromo-3-methoxypyrazine-2-carboxylateHCID 178477796HCID 178477796, 화합물

생성물 1

HCID 22247866Methyl 3-methoxy-6-methylpyrazine-2-carboxylate수율 73%

시약·촉매·용매 4

HCID 178418745HCID 178418745, 화합물촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

After dissolving 300 mg of methyl 6-bromo-3-methoxypyrazine-2-carboxylate in 10 ml of tetrahydrofuran, 32 mg of [1,3-bis(diphenylphosphino)propane]dichloronickel(II) was added, a solution of 0.73 ml of dimethyl zinc in toluene (2.0 M) was added dropwise under a nitrogen atmosphere and the mixture was stirred at room temperature for 3 hours. Saturated aqueous ammonium chloride solution and aqueous sodium carbonate solution were added to the reaction solution in that order, and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (161 mg, 73% yield).

후처리

  1. additionwas added
  2. washThe organic layer was washed with water and saturated brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-3f680eb3d56b4a00b37a63e75ee7937b
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265108B2

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