Triethylamine → Imidazo[1,2-a]pyridine-6-carboxamide,n-[[5-(3-fluorophenoxy)-2-thienyl]methyl]-

HRID 2080006Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=12.[F:13][C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=1)[O:17][C:18]1[S:22][C:21]([CH2:23][NH2:24])=[CH:20][CH:19]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[F:13][C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=1)[O:17][C:18]1[S:22][C:21]([CH2:23][NH:24][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=2)=[O:12])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of imidazo[1,2-a]pyridine-6-carboxylic acid (87 mg, 0.54 mmol) and C-(5-(3-fluorophenoxy)thiophen-2-yl)methylamine (120 mg, 0.54 mmol) in N,N-dimethylformamide (5 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (240 mg, 0.54 mmol) and triethylamine(0.15 mL, 1.08 mmol), and the solution was stirred for 40 minutes at 80° C. Water and ethyl acetate were added to the reaction mixture for extraction, and the organic layer was washed twice with water. Silica gel was added to the organic layer, solvent was evaporated in vacuo for adsorption, purification was carried out by silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate), and the title compound (90 mg, 0.25 mmol, 45.4%) was obtained as a light brown oil.

Workup

washthe organic layer was washed twice with water
additionSilica gel was added to the organic layer, solvent
customwas evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record: ord-336412bd8be14347a47b206ea71aa70e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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