Potassium Carbonate → 3-[2-(4-Fluoro-phenyl)-pyridin-4-yl]-7-[3-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

HRID 383276Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[N:18]4[CH:19]=[CH:20][C:21]([C:23]5[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=5)=[CH:22][C:17]4=[N:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[N:18]4[CH:19]=[CH:20][C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:32][CH2:33][CH2:34][N:35]6[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]6)[CH:24]=5)=[CH:22][C:17]4=[N:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-{3-[2-(4-Fluoro-phenyl)-pyridin-4-yl]-imidazo[1,2-a]pyridin-7-yl}-phenol (Ex. 1.102) (1 eq, 0.131 mmol, 50 mg), 1-(3-chloropropyl)piperidine monohydrochloride (2.0 eq, 0.262 mmol, 53.7 mg) and potassium carbonate (3.0 eq, 0.394 mmol, 54.4 mg) are dissolved in DMF (4 ml) and heated at 60° C. for 16 h. The reaction mixture is diluted with CH2Cl2 and washed with NaHCO3 and brine. The organic phase is dried over MgSO4, filtered and evaporated to dryness. The reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 7/3 to yield 3-[2-(4-fluoro-phenyl)-pyridin-4-yl]-7-[3-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine as a yellow solid; [M+H]+=507

Workup

washwashed with NaHCO3 and brine
dry with materialThe organic phase is dried over MgSO4
filtrationfiltered
customevaporated to dryness
customThe reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 7/3

Sources & evidence

ORD record: ord-98e5661756e741f09696a294b7a185f6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367662B2

Reaction notes

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