5-Bromopyridine-2-carbonitrile → HCID 67253198, compound

HRID 2042044Notes

Reaction equation

HRID 2042044 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].CC(C)([O-])C.[K+].Br[C:17]1[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=1>CC(N(C)C)=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][C:17]1[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 8171545-Bromopyridine-2-carbonitrileHCID 135191803-Amino-4-fluorophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 67253198HCID 67253198, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-amino-4-fluoro-phenol (5.6 g, 44 mmol) in dimethylacetamide (60 mL) was degassed in vacuo and was treated with potassium tert-butoxide (5.3 g, 47 mmol). The resulting solution was stirred for 30 min. 5-Bromo-pyridine-2-carbonitrile (6.6 g, 36 mmol) was added in one-portion and the mixture was heated at 80° C. overnight. The solvent was removed in vacuo and the residue was purified by silica gel chromatography to provide 5-(3-amino-4-fluorophenoxy)picolinonitrile (3.5 g, 44% yield). 1H-NMR (300 MHz, DMSO-d6) δ 8.47 (d, J=3.0 Hz, 1H), 7.98 (d, J=8.4 Hz, 1H), 7.44 (dd, J=8.8, 2.7 Hz, 1H), 7.06 (t, J=9.2 Hz, 1H), 6.52 (d, J=7.6 Hz, 1H), 6.28 (m, 1H), 5.44 (br s, 2H); MS (ESI) m/z: 230.0 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4c5d9578c9534c449779a09a6febad0d
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

Loading…