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2-Methoxyethanol → 5-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

HRID 1159197
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반응식

HRID 1159197 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[NH:7][CH:6]=1)=[O:4].[CH3:13][O:14][CH2:15][CH2:16]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][CH2:16][CH2:15][O:14][CH3:13])=[N:7][CH:6]=1
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참가 물질

6

반응물 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 2764315Methyl 5-bromo-6-hydroxynicotinateHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 675049645-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester수율 45.9%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

5-Bromo-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (15 g, 65 mmol, CA 381247-99-0) was suspended in THF (500 mL). To this suspension was added with stirring 2-methoxyethanol (7.1 mL, 97 mmol), diisopropylazodicarboxylate (21.5 mL, 97 mmol) and triphenylphosphine (25.4 g, 97 mmol). This mixture was stirred for 1 h at room temperature and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica (heptane/ethylacetate, 2:1) to give the title compound (8.65 g) as a yellow solid; MS (ISP) 290.1 (M+H)+.

후처리

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by flash chromatography on silica (heptane/ethylacetate, 2:1)

출처 및 근거

ORD 기록
ord-32cf3f3be186452bb6cac4f60853c8f9
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07812028B2

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