Sodium hydride → HCID 24739707, compound

HRID 1911097Notes

Reaction equation

HRID 1911097 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[C:4]([F:11])[CH:3]=1.Cl[C:13]1[C:18]([CH2:19][C:20]#[N:21])=[CH:17][CH:16]=[CH:15][N:14]=1.[H-].[Na+]>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:18]3[C:19]=2[C:20]#[N:21])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27570034-Bromo-2-fluorophenylisothiocyanateHCID 147395432-(2-Chloropyridin-3-yl)acetonitrile

Product 1

HCID 24739707HCID 24739707, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-2-fluoro-1-isothiocyanatobenzene (250 mg, 1.08 mmol) and (2-chloropyridin-3-yl)acetonitrile (D. H. Bremner et al., Synthesis, 1997, 949) (165 mg, 1.08 mmol) were stirred in DMSO (20 mL) and sodium hydride (52 mg, 1.3 mmol) added portionwise. After evolution of gases had finished the reaction mixture was heated for 4 h at 80° C. After this time the reaction mixture was added to ice (50 mL) and a precipitate formed. This was filtered and purified by preparative HPLC (pH 10, 2-3 min) to give the title compound as a white powder (30 mg, 9%). δH (DMSO-d6) 10.45 (1H, s), 8.31 (1H, d, J 3.9 Hz), 7.75 (2H, m), 7.51-7.38 (3H, m). LCMS (ES+) RT 3.49 minutes, 350 (M+H)+.

Workup

  1. customa precipitate formed
  2. filtrationThis was filtered
  3. custompurified by preparative HPLC (pH 10, 2-3 min)

Sources & evidence

ORD record
ord-36beec6af53c40e1ae10ad3bf9e346e5
Source dataset
uspto-grants-2013_12
Patent number
US08604051B2

Reaction notes

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