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

HRID 226976
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HRID 226976 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][C:12]([CH3:18])=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Br)[N:27]=1>CN(C)C=O>[Br:25][C:26]1[N:27]=[C:28]([CH2:32][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[C:12]([CH3:18])[N:11]=3)[C:16](=[O:17])[C:7]([C:5](=[O:6])[C:4]3[CH:19]=[CH:20][C:21]([CH3:22])=[C:2]([CH3:1])[CH:3]=3)=[CH:8]2)[CH:29]=[CH:30][CH:31]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 577546333-(3,4-Dimethyl-benzoyl)-7-methyl-1H-[1,8]naphthyridin-4-one

생성물 1

HCID 577546491-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-7-methyl-1H-[1,8]naphthyridin-4-one수율 18.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 0.100 g (0.342 mmol) of 3-(3,4-Dimethyl-benzoyl)-7-methyl-1H-[1,8]naphthyridin-4-one, 16.4 mg (0.410 mmol, 60% dispersion in oil) of sodium hydride, 0.103 g (0.410 mmol) of 2-bromo-6-bromomethyl-pyridine and 3.5 mL of N,N dimethylformamide. The crude brown solid was purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 29.5 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-7-methyl-1H-[1,8]naphthyridin-4-one as an off white solid. LC-MSD, m/z for C24H20BrN3O2 [M+H]: 463.07 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.7 min

후처리

  1. customThe crude brown solid was purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA

출처 및 근거

ORD 기록
ord-4af1e7dc26c1428c993e1b53cd72fef5
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557213B2

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