Oxalyl chloride → (6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-acetyl chloride hydrochloride

HRID 858885Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][C:19]([OH:21])=O)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(Cl)(=O)C([Cl:25])=O>ClCCl.CN(C)C=O>[ClH:25].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][C:19]([Cl:25])=[O:21])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a magnetically stirred solution of (6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid 1a (1.0 g, 3.57 mmol) in dichloromethane (DCM) (10.0 mL) at 0° C. under Ar atmosphere were added dimethylformamide (DMF) (1 drop) and oxalyl chloride (0.467 mL, 5.35 mmol). The reaction mixture was stirred at 0° C. for 3 h, then concentrated in vacuo to provide the title compound (1.06 g, 100%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 2.42 (s, 3H), 2.52 (s, 3H), 4.70 (s, 2H), 7.38 (d, J=7.3 Hz, 2H), 7.64 (m, 3H), 8.00 (s, 1H), 8.37 (d, J=8.0 Hz, 1H).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a17d82181e0e4fc0b5be3b2b59802723
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148353B2

Reaction notes

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