Sodium Carbonate → HCID 136510998、化合物

HRID 595553ノート

反応式

HRID 595553 の反応式
[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

参加物

4

反応物 3

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

生成物 1

HCID 136510998HCID 136510998、化合物収率 37%

反応条件

温度
120 °C

実験手順

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.

後処理

  1. filtrationThen the mixture was filtrated

出典と根拠

ORDレコード
ord-6983b27c72d9473cb473d34c6ce80700
出典データセット
uspto-grants-2016_01
特許番号
US09242998B2

反応ノート

読み込み中…