Sodium Carbonate → HCID 136510998, compound

HRID 595553Notes

Reaction equation

HRID 595553 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 136510998HCID 136510998, compoundYield 37%

Conditions

Temperature
120 °C

Procedure

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.

Workup

  1. filtrationThen the mixture was filtrated

Sources & evidence

ORD record
ord-6983b27c72d9473cb473d34c6ce80700
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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