Water → HCID 178458528, compound

HRID 1644601Notes

Reaction equation

HRID 1644601 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH:29]([CH3:31])[CH3:30])=[C:13]([C:15]2[NH:27][C:18]3=[N:19][C:20]([C:23](OC)=[O:24])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH:29]([CH3:31])[CH3:30])=[C:13]([C:15]2[NH:27][C:18]3=[N:19][C:20]([CH2:23][OH:24])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178497319HCID 178497319, compound

Product 1

HCID 178458528HCID 178458528, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridine-5-carboxylate (0.45 g) in tetrahydrofuran (10 ml) was added lithium aluminum hydride (82 mg) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, and water was added. The insoluble material was removed by filtration, and the filtrate was concentrated to give the title compound (0.26 g, yield 61%) as colorless crystals. melting point 167-168° C. purity 99%. M+H: 390. 1H NMR (CDCl3) δ: 1.52 (6H, d, J=6.0 Hz), 4.74-4.82 (1H, m), 5.16 (2H, s), 7.00-7.50 (8H, m), 8.06 (1H, d, J=8.1 Hz), 8.19 (1H, d, J=3.0 Hz).

Workup

  1. temperaturecooling
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3c7acf04a8ef4ddbad566127cb65e527
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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