Sodium hydride → HCID 60204509, compound

HRID 2267388Notes

Reaction equation

HRID 2267388 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.Br[C:11]1[S:12][CH:13]=[CH:14][N:15]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[C:13]2[S:12][CH:11]=[N:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680244-Fluoro-N-methylanilineHCID 764302-Bromothiazole

Product 1

HCID 60204509HCID 60204509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g (40 mmol) of 4-fluoro-N-methylaniline and 3.6 mL (40 mmol) of 2-bromothiazole were added to a suspension of 1.9 g (81 mmol) of NaH in 100 mL of DMF, and the suspension was stirred overnight at rt. The reaction mixture was concentrated onto 20 g of silica in vacuo and the residue purified by flash chromatography eluting with a linear gradient of 20% EtOAc in hexane to 100% EtOAc to deliver the desired compound. MS (M+H)+ 209.

Workup

  1. concentrationThe reaction mixture was concentrated onto 20 g of silica in vacuo
  2. customthe residue purified by flash chromatography
  3. washeluting with a linear gradient of 20% EtOAc in hexane to 100% EtOAc

Sources & evidence

ORD record
ord-27075876577f46d285a19496506b2284
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…