Methyl 2-(2-(3-bromophenyl)-5-chloro-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetate → Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetate

HRID 1481996Notes

Reaction equation

HRID 1481996 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH3:16])[C:13]([C:17](=[O:22])[C:18]([O:20][CH3:21])=[O:19])=[C:12](Cl)[N:11]3[CH:24]=2)[CH:5]=[CH:6][CH:7]=1.C(C1(C)CCN([C:35]2[N:40]3C=C(C(OCC)=O)N=[C:39]3[CH:38]=[C:37]([CH3:49])[C:36]=2C(=O)C(OC)=O)CC1)CC=C>>[CH2:18]([O:19][C:37]1([CH3:49])[CH2:36][CH2:35][N:40]([C:12]2[N:11]3[CH:24]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=4)[N:9]=[C:10]3[CH:15]=[C:14]([CH3:16])[C:13]=2[C:17](=[O:22])[C:18]([O:20][CH3:21])=[O:19])[CH2:39][CH2:38]1)[CH:17]=[CH2:13]

Participants

3

Reactant 2

HCID 118308817Methyl 2-(2-(3-bromophenyl)-5-chloro-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetateHCID 118308840Ethyl 5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(2-methoxy-2-oxoacetyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 118308795Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetateYield 77%

Procedure

Prepared from methyl 2-(2-(3-bromophenyl)-5-chloro-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetate in 77% yield following the same procedure as ethyl 5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(2-methoxy-2-oxoacetyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate. 1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 8.00 (s, 1H), 7.93 (d, J=7.6 Hz, 1H), 7.53-7.49 (m, 1H), 7.41 (br. s., 1H), 7.34 (t, J=7.8 Hz, 1H), 6.24-6.09 (m, 1H), 5.53 (d, J=16.9 Hz, 1H), 5.41 (d, J=10.2 Hz, 1H), 4.03-4.00 (m, 2H), 3.97 (s, 3H), 3.86 (t, J=11.3 Hz, 2H), 2.81 (d, J=7.6 Hz, 2H), 2.42 (s, 3H), 1.96 (d, J=12.6 Hz, 2H), 1.64 (br. s., 2H), 1.32 (s, 3H); LCMS (ESI, M+1): 526.2.

Sources & evidence

ORD record
ord-b613779caa1d4f10abaa0489fbd4e104
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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