Potassium Phosphate, Tribasic → 6-[4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 912514Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[CH:11][N:12]([CH3:13])[C:4]=2[CH:3]=1.[OH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][C:19]=1[C:27]([F:30])([F:29])[F:28].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[N:7]=[C:6]([C:8]#[N:9])[C:5]3[N:10]=[CH:11][N:12]([CH3:13])[C:4]=3[CH:3]=2)=[CH:20][C:19]=1[C:27]([F:28])([F:29])[F:30]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloro-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (0.75 g), 4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenylboronic acid (1.46 g), tris(dibenzylideneacetone)dipalladium (0.18 g), tricyclohexylphosphine (0.13 g) and tribasic potassium phosphate (1.65 g) in dioxane (7.5 ml) and water (3 ml) was heated at 100° C. under N2 for 3 hours. The mixture was then diluted with ethyl acetate (100 ml), organic layer seperated and solvent removed under reduced pressure, the residue was then columned on silica gel using DCM-MeOH (3%) as eluant to give 6-[4-(2-hydroxyethoxy)-3-(trifluoromethyl)-phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (1.07 g).

Workup

customseperated
customsolvent removed under reduced pressure

Sources & evidence

ORD record: ord-9b462c240f1e4d06af0d13e67c4218cf
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026236B2

Reaction notes

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