Sodium Hydroxide → 3-(5-indolyl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

HRID 1886455Notes

Reaction equation

C([N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][N:19]3[C:23]4=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]4[N:21]=[C:20]3[CH2:30][CH3:31])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][N:19]3[C:23]4=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]4[N:21]=[C:20]3[CH2:30][CH3:31])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of the product of Example 1 (500 mg, 1.225 mmol) in 10 ml of methanol was added 10 ml of 2N NaOH and the mixture heated to 60° C. After 18 hours the methanol was removed in vacuo. The reaction mixture was diluted with 150 mL of H2O and extracted with 3×200 mL of CH2Cl2. The combined extracts were dried over Na2SO4, filtered and concentrated to yield by the titled compound (377 mg, 100%) as a pale yellow powder.

Workup

customAfter 18 hours the methanol was removed in vacuo
additionThe reaction mixture was diluted with 150 mL of H2O
extractionextracted with 3×200 mL of CH2Cl2
dry with materialThe combined extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d2fb6dfbdef14ed6b6525ef23b2887db
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05151435

Reaction notes

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