Sodium hydride → HCID 69374878, compound

HRID 860991Notes

Reaction equation

HRID 860991 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][SH:17])=[CH:12][CH:11]=1.[H-].[Na+]>CN(C=O)C.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([S:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 85171p-Fluorotoluene-alpha-thiol

Product 1

HCID 69374878HCID 69374878, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-dibromopyridine (1.0 eq.) and (4-fluoro-phenyl)-methanethiol (1.2 eq.) in DMF (0.2M) at 0° C. was added portionwise NaH (1.3 eq.). The mixture was stirred for 1 h at rt, poured in water and extracted with Et2O. The organic extract was washed with water (2×), brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1) afforded the title compound as a yellow solid.

Workup

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with water (2×), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9efd5e15fabe4c93ad7e68e9824c6bbf
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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