Potassium Carbonate → 3-(Benzo[d]thiazol-2-yl)-6-fluoroimidazo[1,2-a]pyridin-2-amine

HRID 1473950Notes

Reaction equation

FC(F)(F)C([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]2[CH:15]=1)=O.Br[C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[C:15]1[N:9]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]2=[N:7][C:6]=1[NH2:5]

Participants

Conditions

Temperature: 100 °C

Procedure

2,2,2-Trifluoro-N-(6-fluoro-imidazo[1,2-a]pyridin-2-yl)-acetamide (compound c, 6 g, 0.02 mol), 2-bromo-1,3-benzothiazole (6.8 g, 32 mmol), potassium carbonate (7000 mg, 0.05 mol), and triphenylphosphine (1000 mg, 0.005 mol) were diluted with 60 ml of a 2:1 solution of dioxane/ethanol and treated with palladium acetate (500 mg, 0.002 mol). The reaction was heated at 100° C. overnight. The reaction was cooled and resulting solid was filtered and washed with dichloromethane then dried to give 3-(benzo[d]thiazol-2-yl)-6-fluoroimidazo[1,2-a]pyridin-2-amine as a yellow solid. Rf 0.37, 70% ethyl acetate/hexanes; MS m/z 285 (M+H).

Workup

temperatureThe reaction was cooled
customresulting solid
filtrationwas filtered
washwashed with dichloromethane
customthen dried

Sources & evidence

ORD record: ord-c64aed2daf9048aab376478426936cb9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018208B2

Reaction notes

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