Benzene, 1-iodo-3-(trifluoromethyl)- → 5-methyl-7-phenyl-N-(3-(trifluoromethyl)phenyl)imidazo[1,5-f][1,2,4]triazin-2-amine
Reaction equation
Cl.[CH3:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH2:12])=[N:7]2.I[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>O1CCOCC1.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]>[CH3:2][C:3]1[N:4]=[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH:12][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)=[N:7]2Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
In a similar manner as described for Example 25, 5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride (26 mg, 0.1 mmol), 1-iodo-3-(trifluoromethyl)benzene (33 mg, 0.12 mmol), tris(dibenzylideneacetone)dipalladium (10 mg, 0.01 mmol), 2-(di-t-butylphosphino)biphenyl (10 mg, 0.03 mmol) and sodium t-butoxide (25 mg, 0.23 mmol) in dioxane (0.80 mL) gave 5-methyl-7-phenyl-N-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (30 mg, 81%) as a yellow solid. 1H NMR (CDCl3): δ8.83 (s, 1H), 8.46-8.49 (m, 2H), 8.33 (s, 1H), 7.43-7.57 (m, 5H), 7.35 (d, J=7.51 Hz, 1H), 7.08 (s, 1H), 2.63 (s, 3H). MS m/z 369 (M+1).
Sources & evidence
- ORD record
- ord-9892c347e102449380fa1260098b68a1
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462614B2
Reaction notes
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