Water → HCID 66846594, compound

HRID 254167Notes

Reaction equation

HRID 254167 reaction equation
[CH3:1][NH:2][C:3](=[O:5])[CH3:4].[H-].[Na+].Br[CH2:9][C:10]1[N:15]=[C:14]([C:16]#[N:17])[C:13]([CH3:18])=[CH:12][CH:11]=1.O>C1COCC1>[C:16]([C:14]1[N:15]=[C:10]([CH2:9][N:2]([CH3:1])[C:3](=[O:5])[CH3:4])[CH:11]=[CH:12][C:13]=1[CH3:18])#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6582N-MethylacetamideHCID 24758Sodium hydrideHCID 668466086-(Bromomethyl)-3-methyl-2-pyridinecarbonitrile

Product 1

HCID 66846594HCID 66846594, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methylacetamide (416 mg, 5.69 mmol) in THF (15 mL) at room temperature was treated with NaH (228 mg, 5.69 mmol), stirred for 15 min, treated with 6-bromomethyl-3-methylpyridine-2-carbonitrile (1.0 g, 4.74 mmol), stirred for 16 h, poured into water (50 mL), extracted with EtOAc (3×15 mL) and the combined organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (665 mg, 69%) as a yellow oil; NMR δH (400 MHz, CDCl3) 2.15 (3H, s), 2.53 (3H, s), 3.09 (3H, s), 4.65 (2H, s), 7.43 (1H, d, J 8.0 Hz) and 7.61 (1H, d, J 8.0 Hz); M/Z 204 (M+H)+

Workup

  1. stirringstirred for 16 h
  2. extractionextracted with EtOAc (3×15 mL)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42e81c4e5a0e424ba8718db1cf98d0ff
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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