2-Aminopyridine → 2-Ethylimidazo[1,2-a]pyridine

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10](=O)[CH2:11][CH3:12].C(OC(N1CCC(CC(Br)=O)CC1)=O)(C)(C)C>>[CH2:11]([C:10]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[CH:9]=1)[CH3:12]

Participants

Reactant 3

HCID 104392-Aminopyridine

HCID 131561-Bromo-2-butanone

HCID 184611401-t-Butyloxycarbonyl-4-(1-bromo-formylmethyl)piperidine

Product 1

HCID 218319912-Ethylimidazo[1,2-a]pyridine

Procedure

The title compound was prepared from 2-aminopyridine and 1-bromo-2-butanone, employing procedures analogous to those described for Piperidine 1. 1H NMR (500 MHz, CDCl3) δ 1.34 (t, J=7.3 Hz, 3H), 2.82 (q, J=7.6 Hz, 2H), 6.70 (t, J=6.6 Hz, 1H), 7.10 (m, 1H), 7.32 (s, 3H), 7.51 (d, J=8.9 Hz, 1H), 8.03 (dd, J=6.6, 0.9 Hz, 1H).

Sources & evidence

ORD record: ord-9f493c7dd14d4f50bcec6bf170509ef8
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125887B2

Reaction notes

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