Sodium hydride → HCID 10251994, compound

HRID 1492612Notes

Reaction equation

HRID 1492612 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[N:14][C:15]([CH3:19])=[CH:16][C:17]([CH3:18])=[C:12]3[N:11]=[C:10]2[CH2:20][CH3:21])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Br[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][C:34]([O:36][CH3:37])=[O:35]>CN(C=O)C>[C:34]([CH:33]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[N:14][C:15]([CH3:19])=[CH:16][C:17]([CH3:18])=[C:12]3[N:11]=[C:10]2[CH2:20][CH3:21])=[CH:4][CH:3]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:27]=1)([O:36][CH3:37])=[O:35]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 100165294-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 10251994HCID 10251994, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.50 g (1.79 mmol) of 3-(4-aminophenylmethyl) -5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine (Step B, Example 25) in 4.0 mL DMF, was added 143 mg (3.57 mmol, 2.0 eq) of a 60% oil dispersion of NaH. When evolution of hydrogen ceased (approximately 5 min.), 1.04 mL (5.36 mmol, 3.0 eq) of methyl 2-bromophenylacetate was added, and the mixture was stirred for 18 hours. The DMF was removed in vacuo and the resultant brown oil was flash chromatographed with 2:1 ethyl acetate/hexane to yield 0.690 g (90%) of a yellow-green powder.

Workup

  1. additionwas added
  2. customThe DMF was removed in vacuo
  3. customchromatographed with 2:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-541cd182b3e34d5aaf68f1a02e944fb7
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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