N-(3-bromo-4-methoxyphenyl)acetamide → N-[4-methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamide

HRID 2374941Notes

Reaction equation

HRID 2374941 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH2:11])=[N:6]2.Br[C:23]1[CH:24]=[C:25]([NH:31][C:32](=[O:34])[CH3:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC([O-])(C)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]>[CH3:30][O:29][C:28]1[CH:27]=[CH:26][C:25]([NH:31][C:32](=[O:34])[CH3:33])=[CH:24][C:23]=1[NH:11][C:7]1[N:8]=[CH:9][C:10]2=[C:2]([CH3:1])[N:3]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=3)[N:5]2[N:6]=1

Participants

7

Reactant 4

HCID 244158N-(3-bromo-4-methoxyphenyl)acetamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 587120012-Amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin2×

Product 1

HCID 58711948N-[4-methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamideYield 17%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

In a similar manner as described for Example 41, 5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (intermediate 45) (0.025 g, 0.09 mmol), N-(3-bromo-4-methoxyphenyl)acetamide (0.044 g, 0.18 mmol), Pd2(dba)3 (0.008 g, 0.01 mmol), 2-(Di-t-butylphosphino)biphenyl (0.008 g, 0.03 mmol), and NaOtBu (0.011 g, 0.11 mmol) in 1,4-dioxane (1 mL) gave N-[4-methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamide (0.007 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.15 (s, 1H), 9.06 (bs, 1H), 8.98 (d, J=7.6 Hz, 1H), 8.73 (s, 1H), 8.53 (d, J=2.4 Hz, 1H), 7.83-7.70 (m, 3H), 7.30 (dd, J=8.7, 2.3 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 3.94 (s, 3H), 2.59 (s, 3H), 2.09 (s, 3H). MS m/z 457 (M+1).

Sources & evidence

ORD record
ord-d402674f14c547b08e22414eba5cf0a8
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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