2-(3-Bromophenyl)ethan-1-ol → 2-[3-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]ethanol

HRID 2374942Notes

Reaction equation

HRID 2374942 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]([CH2:29][CH2:30][OH:31])[CH:26]=[CH:27][CH:28]=1.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]>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:11][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][OH:31])[CH:26]=[CH:27][CH:28]=1)=[N:6]2

Participants

7

Reactant 4

HCID 27340902-(3-Bromophenyl)ethan-1-olHCID 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 113844032-[3-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]ethanolYield 53.8%

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), 2-(3-bromophenyl)ethanol (0.012 mL, 0.09 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 2-[3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]ethanol (0.020 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.13 (s, 1H), 8.91 (d, J=7.9 Hz, 1H), 8.85 (s, 1H), 8.74 (bs, 1H), 7.89-7.75 (m, 3H), 7.76 (s, 1H), 7.33 (dd, J=7.8, 7.8 Hz, 1H), 7.22 (s, 1H), 7.00 (d, J=7.7 Hz, 1H), 3.81 (t, J=7.0 Hz, 2H), 2.87 (t, J=7.0 Hz, 2H), 2.57 (s, 3H). m/z 414 (M+1).

Sources & evidence

ORD record
ord-0df8cd73d9f44b8aa82b38fb76153c93
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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