Lithium Chloride → HCID 136510998, compound

HRID 595554Notes

Reaction equation

HRID 595554 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:10]=3[N:9]=2)[C:5]([O:18]C)=[CH:4][CH:3]=1.[Li+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:10]=3[N:9]=2)[C:5]([OH:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 90333459HCID 90333459, compound

Product 1

HCID 136510998HCID 136510998, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(6-bromo-3-methoxypyridin-2-yl)-4-fluoro-1H-benzo[d]imidazole (350 mg, 1.12 mmol) in DMF (10 mL) was added LiCl (650 mg, 15.5 mmol) under N2 protection. The mixture was stirred on a pre-heated oil-bath at 100° C. overnight. After extracted with EtOAc, the organic phase was dried over Na2SO4 and concentrated. The residue was purified by prep-TLC (PE:EA=5:1) to give the product of 6-bromo-2-(4-fluoro-1H-benzo[d]imidazol-2-yl)pyridin-3-ol (200 mg, yield: 60%). 1H-NMR (DMSO-d6, 400 MHz) δ 13.75 (s, 1H), 12.70 (s, 1H), 7.64 (d, J=8.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.41 (s, 1H), 7.30 (s, 1H), 7.12 (s, 1H). MS (M+H)+: 308/310.

Workup

  1. extractionAfter extracted with EtOAc
  2. dry with materialthe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC (PE:EA=5:1)

Sources & evidence

ORD record
ord-8b3756bf66b1411989ac5ffd44a5df7b
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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