4-Hydroxybenzaldehyde → Benzaldehyde,4-[(3-methyl-3h-imidazo[4,5-b]pyridin-2-yl)methoxy]-

HRID 356337Notes

Reaction equation

HRID 356337 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1[CH2:11][OH:12].O[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH:18]([C:17]1[CH:20]=[CH:21][C:14]([O:12][CH2:11][C:3]2[N:2]([CH3:1])[C:6]3[C:5]([N:4]=2)=[CH:10][CH:9]=[CH:8][N:7]=3)=[CH:15][CH:16]=1)=[O:19]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 10702152(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

Product 1

HCID 23298364Benzaldehyde,4-[(3-methyl-3h-imidazo[4,5-b]pyridin-2-yl)methoxy]-Yield 45.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A procedure similar to that described in Preparation 4 was repeated, except that 500 mg of 3-methylimidazo-[5,4-b]pyridin-2-ylmethanol (prepared as described in Preparation 15), 374 mg of 4-hydroxybenzaldehyde, 0.76 ml of tributylphosphine, 773 mg of 1,1'-(azo-dicarbonyl)dipiperidine and 12 ml of toluene were used, and that the product was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of ethyl acetate and methanol in ratios ranging from 1:0 to 50:1 by volume as the eluent, to give 0.37 g of the title compound, melting at 124°-125° C.

Workup

  1. customA procedure similar to that described in Preparation 4
  2. customthat the product was purified by column chromatography through silica gel
  3. washa gradient elution method

Sources & evidence

ORD record
ord-0ef2787331dc4d06adea043114f913fa
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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