Sodium hydride → HCID 178490686, compound

HRID 78535

Reaction equation

HRID 78535 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[S:11][C:12]([CH3:15])=[CH:13][N:14]=1)=[O:8].[H-].[Na+].Br[CH2:22][C:23]1[O:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7](/[N:9]=[C:10]1\[S:11][C:12]([CH3:15])=[CH:13][N:14]\1[CH2:22][C:23]1[O:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1)=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 26781445-chloro-2-methoxy-N-(5-methyl-1,3-thiazol-2-yl)benzamideHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furan

Product 1

HCID 178490686HCID 178490686, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 340A (0.1 g, 0.36 mmol) in 5 mL DMF was added sodium hydride (0.01 g, 0.39 mmol, 95%). The solution was allowed to stir at ambient temperature for 30 min when 2-(bromomethyl)-5-(trifluoromethyl)furan (0.09 g, 0.39 mmol) was added. The reaction was held at ambient temperature overnight and then quenched with water. The crude was extracted with ethyl acetate and the organics washed with water, then dried over MgSO4, filtered, and concentrated. Flash chromatography over silica gel (50% ethyl acetate/hexane) gave 0.05 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.28 (d, J=1.36 Hz, 3H) 3.78 (s, 3H) 5.47 (s, 2H) 6.66 (d, J=2.71 Hz, 1H) 7.11 (d, J=8.81 Hz, 1H) 7.22 (dd, J=3.39, 1.36 Hz, 1H) 7.31-7.39 (m, J=1.36 Hz, 1H) 7.41-7.52 (m, 1H) 7.72 (d, J=2.71 Hz, 1H). m/z 431.0 (M+H)+.

Workup

  1. additionwas added
  2. customquenched with water
  3. extractionThe crude was extracted with ethyl acetate
  4. washthe organics washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8ca9a4cfb645472fa09ff1253df89873
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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