Sodium hydride → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one

HRID 226978

반응식

HRID 226978 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[C:11]([CH3:19])[N:12]=[C:13]([CH3:18])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].[Br:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Br)[N:28]=1>CN(C)C=O>[Br:26][C:27]1[N:28]=[C:29]([CH2:33][N:9]2[C:10]3[C:15](=[CH:14][C:13]([CH3:18])=[N:12][C:11]=3[CH3:19])[C:16](=[O:17])[C:7]([C:5](=[O:6])[C:4]3[CH:20]=[CH:21][C:22]([CH3:23])=[C:2]([CH3:1])[CH:3]=3)=[CH:8]2)[CH:30]=[CH:31][CH:32]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 577547743-(3,4-Dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one

생성물 1

HCID 577547291-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one수율 12.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Experimental conditions analogous to described for Step 3 of Example 1 were used with 42 mg (0.137 mmol) of 3-(3,4-Dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one, 6 mg (0.165 mmol, 60% dispersion in oil) of sodium hydride, 41.3 mg (0.165 mmol) of 2-bromo-6-bromomethyl-pyridine and 1.5 mL of N,N-dimethylformamide. The crude brown solid was purified by flash column chromatography using 30-100% ethyl acetate in hexane to yield 7.9 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one as an off white solid. LC-MSD, m/z for C25H22BrN3O2 [M+H]: 477.37 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.9 min

후처리

  1. customThe crude brown solid was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-c7462869f20d466fbc008b61ea7225a6
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557213B2

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