Triethylamine → 6-Bromo-2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

HRID 1416293

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:24]3[CH2:23][CH2:22][N:21]([C:15]4[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=4[Cl:13])[CH2:26][CH2:25]3)[N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-bromo-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 15, Step 1; 0.582 g), 1-(2,4-dichlorophenyl)piperazine (Example 31, Step 1; 0.548), triethylamine (Aldrich; 0.288 g), and THF (5 mL) is stirred at 80° C. for 6 h, at which time it is cooled and then partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. Chromatography of the residue on silica gel using methanol/dichloromethane (2/98) and crystallization gives 0.710 g of the title compound; mp 137-138° C.; MS m/z 438, 440; IR (mineral oil) 1479, 1341, 1058, 2810, 803 cm-1. 1H NMR (CDCl3) δ2.78, 3.09, 3.80, 6.96, 7.16-7.23, 7.35, 7.48, 7.55, 8.24.

Workup

temperatureis cooled
custompartitioned between dichloromethane and aq. sodium bicarbonate
dry with materialThe organic layers are dried over sodium sulfate
concentrationconcentrated
custommethanol/dichloromethane (2/98) and crystallization

Sources & evidence

ORD record: ord-e85312339b5a4fbbaac35fb43cdd60ce
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912246

Linked notes

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