Dimethylformamide → HCID 86745619, compound

HRID 1029598Notes

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

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-butyllithium (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 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. 1H NMR (300 MHz, CD3OD) δ8.25 (s, 1H), 7.59-7.41 (m, 4H), 7.18-7.09 (ABq, 4H), 5.52 (s, 2H), 4.79 (s, 2H), 2.83 (t, 2H, J=7.5 Hz), 2.70 (s, 3H), 1.78-1.63 (m, 2H), 0.96 (t, 3H, J=7.5 Hz).

Workup

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

Sources & evidence

ORD record: ord-15def3ba00534155be474c0adc8ef411
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102880

Reaction notes

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