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

HRID 1624107Notes

Reaction equation

[OH:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.I[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:12][C:10]1[N:11]=[C:3]2[C:2]([O:1][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]2[C:9]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

2.0 g (8.5 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 87A were initially charged in 122.3 ml of DMF, and 1.23 ml (9.4 mmol) of 1-iodo-3-methylbutane and 6.12 g (18.8 mmol) of caesium carbonate were added. The mixture was stirred at 60° C. for 40 min. The reaction mixture was cooled to RT, 900 ml of water were added and the mixture was stirred at RT for 1 h. 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

temperatureThe reaction mixture was 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-d189b549c7ba4657952254d62b737812
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778964B2

Reaction notes

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