Water → HCID 59729920, compound

HRID 492558Notes

Reaction equation

HRID 492558 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-f9901d1038e44a729492d93e631ba4a3
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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