Dimethylformamide → HCID 86745619, compound

HRID 466726Notes

Reaction equation

HRID 466726 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:7]([N:14]=1)=[N:8][CH:9]=[C:10](Br)[C:11]=2[CH3:12])[CH2:2][CH3:3].C([Li])(C)(C)C.CN(C)[CH:22]=[O:23]>C1COCC1>[CH2:1]([C:4]1[N:5]=[C:6]2[CH:11]([CH3:12])[C:10]([CH:22]=[O:23])=[CH:9][N:8]=[C:7]2[N:14]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19012220HCID 19012220, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86745619HCID 86745619, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (-78° C.) stirred solution of 2-propyl-6-bromo-7-methylimidazo[4,5-b]pyridine (540 mg, 2.15 mmol) in THF (20 mL) was added tert-butyl-lithium (4.40 mL, 1.7M/pentane) over 30 seconds After 45 minutes, dimethylformamide (0.665 mL) was added and after 10 additional minutes the reaction was warmed to RT and quenched with 20% aqueous 4 NH4Cl. Extractive workup EtOAc (4×10 mL) and purification (SiO2, 4% MeOH/EtOAc) gave 2-propyl-7-methylimidazo[4,5-b]pyridine-6-carboxaldehyde (350 mg). To a stirred, cooled (0° C.) methanolic (15 mL) solution of the aldehyde (300 mg) was added NaBH4 (84 mg). After 30 minutes HOAc (0.1 mL) was added, the mixture was warmed (RT), concentrated, and purified (SiO2, 10% MeOH/CH2Cl2) to give 190 mg of 6-hydroxymethyl-7-methyl-2-propylimidazo[4,5-b]pyridineas an oil. The title compound was prepared by using a similar method to that described in Example 7, Part B.

Workup

  1. temperatureafter 10 additional minutes the reaction was warmed to RT
  2. customquenched with 20% aqueous 4 NH4Cl
  3. customExtractive workup EtOAc (4×10 mL) and purification (SiO2, 4% MeOH/EtOAc)

Sources & evidence

ORD record
ord-9d7b3c0901234d9f9f33cbf3b43b0281
Source dataset
uspto-grants-1992_10
Patent number
US05157026

Reaction notes

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