Stannane, tributyl(1-ethoxyethenyl)- → 6-(1-ethoxyvinyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine

HRID 2409050Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH:9]=[N:10][C:4]=2[CH:3]=1.C([Sn](CCCC)(CCCC)[C:25]([O:27][CH2:28][CH3:29])=[CH2:26])CCC>CN1C(=O)CCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:28]([O:27][C:25]([C:2]1[N:7]=[CH:6][C:5]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH:9]=[N:10][C:4]=2[CH:3]=1)=[CH2:26])[CH3:29]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine (500 mg, 1.83 mmol), tributyl(1-ethoxyvinyl)stannane (866 mg, 2.40 mmol), Pd (PPh3)4 (243 mg, 0.27 mmol) in NMP (10 mL) was heated at 140° C. for 72 h. The reaction mixture was quenched with water and extracted with EtOAc (50 mL×3). The combined extracts were washed with water (100 mL) and brine (50 mL), dried (MgSO4) filtered and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with 3% MeOH/DCM to afford 440 mg (78%) of 6-(1-ethoxyvinyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine as a gray solid. MS (EST): m/z=310.3 [M+1]+.

Workup

customThe reaction mixture was quenched with water
extractionextracted with EtOAc (50 mL×3)
washThe combined extracts were washed with water (100 mL) and brine (50 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by SiO2 chromatography
washeluting with 3% MeOH/DCM

Sources & evidence

ORD record: ord-6fc7da3819b348ca93575def14e7fff3
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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