Sodium Carbonate → HCID 136510998, 화합물

HRID 595553노트

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HRID 595553 반응식
[Br:1][C:2]1[N:7]=[C:6]([C:8](O)=O)[C:5]([O:11]C)=[CH:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[C:15]=1[NH2:21].C([O-])([O-])=O.[Na+].[Na+]>>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[NH:20][C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[C:15]=3[N:21]=2)[C:5]([OH:11])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 10340Sodium CarbonateHCID 27828353-Fluorobenzene-1,2-diamineHCID 714639656-Bromo-3-methoxypicolinic acid

생성물 1

HCID 136510998HCID 136510998, 화합물수율 37%

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온도
120 °C

실험 절차

A mixture of 6-bromo-3-methoxypicolinic acid (1.84 g, 7.93 mmol) and 3-fluorobenzene-1,2-diamine (1.0 g, 7.93 mmol) was stirred in PPA (3 mL) on a pre-heated oil-bath at 120° C. for 14 h. The mixture was poured to ice-water and basified to pH=8 with Na2CO3. Then the mixture was filtrated to collect the brown solid as 6-bromo-2-(4-fluoro-1H-benzo[d]imidazol-2-yl)pyridin-3-ol (900 mg, yield: 37%). The filtrated was extracted with ethyl acetate, and the organic layer was washed with brine and dried over Na2SO4. After concentrated, the residue was purified by column chromatography to give the product of 2-(6-bromo-3-methoxypyridin-2-yl)-4-fluoro-1H-benzo[d]imidazole (350 mg, yield: 14%). 1H-NMR (CDCl3, 400 MHz) δ 10.43˜10.56 (m, 1H), 7.46 (d, J=8.8 Hz, 1H), 7.33 (d, J=8.8 Hz, 1H), 7.21˜7.30 (m, 2H), 6.90˜6.98 (m, 1H), 4.05 (s, 3H). MS (M+H)+: 322/324.

후처리

  1. filtrationThen the mixture was filtrated

출처 및 근거

ORD 기록
ord-6983b27c72d9473cb473d34c6ce80700
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242998B2

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