Tetramethyltin → 1-Benzyl-5-hydroxy-3-methyl-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

HRID 919659노트

반응식

HRID 919659 반응식
[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9](Br)=[CH:8]2)=[O:4].[CH3:25][Sn](C)(C)C>CN(C=O)C.[Cl-].[Na+].O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([CH3:25])=[CH:8]2)=[O:4]

참가 물질

7

반응물 2

HCID 11661Tetramethyltin2회HCID 682974771-Benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

생성물 1

HCID 682971641-Benzyl-5-hydroxy-3-methyl-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester수율 74.1%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

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온도
120 °C

실험 절차

A mixture of 1-benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (204 mg, 0.52 mmol), tetramethyltin (0.22 mL, 1.57 mmol), and PdCl2(PPh3)2 (74 mg, 0.10 mmol) in 5 mL of DMF was heated at 120° C. for 1 h under N2 atmosphere. Additional tetramethyltin (0.22 mL, 1.57 mmol) was added and the mixture was heated for 1 h at the same temperature. The mixture was cooled to r.t. and diluted with brine (10 mL) and EtOAc (40 mL). The aqueous layer was extracted with additional EtOAc, and the combined organic layer was washed with water and dried over MgSO4. After the solvent was evaporated in vacuo, the crude residue was chromatographed (0-60% EtOAc/hexanes+2% AcOH) to give 125 mg of the title compound as a pale yellow solid. MS: (+) m/z 325.05 (M+1).

후처리

  1. temperaturethe mixture was heated for 1 h at the same temperature
  2. temperatureThe mixture was cooled to r.t.
  3. extractionThe aqueous layer was extracted with additional EtOAc
  4. washthe combined organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customAfter the solvent was evaporated in vacuo
  7. customthe crude residue was chromatographed (0-60% EtOAc/hexanes+2% AcOH)

출처 및 근거

ORD 기록
ord-92bbfe47fed34baa8ddaa19a51390b72
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09271970B2

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