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Water → 2-{[2-(Benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline-8-carbonitrile

HRID 577482
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HRID 577482 반응식
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19](I)[C:20]([O:26][CH3:27])=[CH:21][CH:22]=3)[C:17]2=[O:29])=[C:13]([CH3:30])[CH:12]=[C:11]([CH3:31])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([Cu])#[N:33].O>CN1C(=O)CCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([C:32]#[N:33])[C:20]([O:26][CH3:27])=[CH:21][CH:22]=3)[C:17]2=[O:29])=[C:13]([CH3:30])[CH:12]=[C:11]([CH3:31])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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6

반응물 3

HCID 962WaterHCID 867237072-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-iodo-7-methoxy-3,4-dihydroisoquinolin-1(2H)-oneHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 867237082-{[2-(Benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline-8-carbonitrile수율 100%

시약·촉매·용매 2

HCID 8857
Ethyl Acetate
용매
HCID 13387N-methyl-2-pyrrolidone용매

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온도
190 °C

실험 절차

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-iodo-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (53c, 300 mg, 0.568 mmol) in NMP (8 mL, dry) was added CuCN (152 mg, 1.705 mmol) at room temperature. The resulting mixture was stirred at 190° C. for 3 hours. The mixture was cooled to room temperature and H2O (20 mL) was added to the mixture. The mixture was diluted with EtOAc (5×20 mL). The combined organic layers were washed with brine (3×20 mL), dried over Na2SO4, and concentrated under vacuum to give a residue, which was purified by column chromatography (petroleum ether/EtOAc, 3:1) to obtain 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline-8-carbonitrile (53d, ˜0.568 mmol, 100%) as a yellow solid.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washThe combined organic layers were washed with brine (3×20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by column chromatography (petroleum ether/EtOAc, 3:1)

출처 및 근거

ORD 기록
ord-bfd201a7a0db4a2990fe88946f349242
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040515B2

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