Water → Ethyl 2,6-dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylate

HRID 2275854Notes

Reaction equation

I[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:13][C:14]1[C:15]2[N:16]([C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:22]([CH3:24])[N:23]=2)[CH:17]=[C:18]([CH3:20])[CH:19]=1.O>CN(C=O)C>[CH3:24][C:22]1[N:23]=[C:15]2[C:14]([O:13][CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[CH:19][C:18]([CH3:20])=[CH:17][N:16]2[C:21]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

Conditions

Temperature: 60 °C

Procedure

1.23 ml (9.4 mmol) of 1-iodo-3-methylbutane and 6.12 g (18.8 mmol) of caesium carbonate were added to 2.0 g (8.5 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 239A in 122.3 ml of DMF, and the mixture was stirred at 60° C. for 40 min. 900 ml of water were added to the reaction mixture, which had cooled to RT, and the mixture was stirred at RT for 1 h, and the precipitated solid was filtered off, washed with water and dried under high vacuum. This gave 2.25 g (84% of theory; purity 97%) of the title compound.

Workup

temperaturehad cooled to RT
stirringthe mixture was stirred at RT for 1 h
filtrationthe precipitated solid was filtered off
washwashed with water
customdried under high vacuum

Sources & evidence

ORD record: ord-7c94d70165b04209b9dfea512fe420f5
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126998B2

Reaction notes

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