Water → HCID 59729920, compound

HRID 228403Notes

Reaction equation

HRID 228403 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([OH:17])=[C:12]([F:18])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=1.[H-].[Na+].O>CS(C)=O>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([O:17][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)=[C:12]([F:18])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 59730069HCID 59730069, compound

Product 1

HCID 59729920HCID 59729920, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of phenol obtained in step 3 above (1.31 g, 4.8 mmol), 6-chloronicotinonitrile (700 mg, 5.04 mmol) and sodium hydride (290 mg, 7.2 mmol) in DMSO (25 mL) is stirred at room temperature for 18 h. Pour the mixture into iced water and extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4, filtrate and eliminate the solvent. Purify by flash chromatography (EtOAc/hexane 20/80 and 34/66) to get the title compound (950 mg, 51%). 1H-NMR (CDCl3, 200 MHz): 8.41 (dd, 1H, J=0.8 and 2.1 Hz), 7.97 (dd, 1H, J=2.4 and 8.6 Hz), 7.18 (dd, 1H, J=0.8 and 8.6 Hz), 6.92-6.81 (m, 2H), 3.39 (q, 2H, J=6.9 Hz), 2.81 (t, 2H, J=6.7 Hz), 1.45 (s, 9H).

Workup

  1. extractionextract the aqueous layer with EtOAc
  2. dry with materialDry the organic layer over Na2SO4, filtrate
  3. customPurify by flash chromatography (EtOAc/hexane 20/80 and 34/66)

Sources & evidence

ORD record
ord-7fc6d6916b6d43568f0d88eed5d7fb3b
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

Loading…