Sodium hydride → HCID 71257339, compound

HRID 710096Notes

Reaction equation

HRID 710096 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10](=[S:22])[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[F:21].[H-].[Na+]>CN1CCCC1=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[S:22][C:10]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=3[F:21])=[N:9][C:3]=2[CH:4]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 86676950HCID 86676950, compound

Product 1

HCID 71257339HCID 71257339, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

Intermediate 37 (0.48 g, 1.03 mmol) dissolved in N-Methylpyrrolidinone (0.97 ml) and added NaH (52 mg, 2.2 mmol). This mixture was stirred at 140° C. for 3 h. Reaction mixture cooled to rt and diluted with water to obtain the solid. Solid was filtered and dried to obtain the crude. Crude was purified on column chromatography using 60-120 mesh silicagel and DCM as eluent to afford the titled compound (260 mg) as a white solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.71-8.66 (m, 1H), 8.32 (d, J 1.7, 1H), 7.92-7.83 (m, 3H), 7.59 (dd, J 1.8, 8.6, 1H), 3.13 (s, 3H).

Workup

  1. customReaction mixture
  2. temperaturecooled to rt
  3. customto obtain the solid
  4. filtrationSolid was filtered
  5. customdried
  6. customto obtain the crude
  7. customCrude was purified on column chromatography

Sources & evidence

ORD record
ord-467148ccdb914e7c8e1d8bfce81572c0
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

Loading…