2-(Di-tert-butylphosphino)biphenyl → HCID 11179187, compound

HRID 2374950Notes

Reaction equation

HRID 2374950 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]([CH2:31][CH2:32][NH:33][C:34](=[O:36])[CH3:35])[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:23]=[CH:24][C:25]([CH2:31][CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[CH:26][C:27]=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 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 587120012-Amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin2×HCID 68870134HCID 68870134, compound

Product 1

HCID 11179187HCID 11179187, compoundYield 69.2%

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) (0.050 g, 0.17 mmol), N-[2-(3-bromo-4-methoxyphenyl)ethyl]acetamide (0.046 g, 0.17 mmol), Pd2(dba)3 (0.016 g, 0.02 mmol), 2-(Di-t-butylphosphino)biphenyl (0.015 g, 0.05 mmol), and NaOtBu (0.033 g, 0.34 mmol) in 1,4-dioxane (2 mL) gave N-{2-[4-methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]-ethyl}acetamide (0.057 g) as a yellow solid. 1H NMR (CDCl3): δ8.85 (s, 1H), 8.80 (d, J=7.7 Hz, 1H), 8.62 (s, 1H), 8.23 (s, 1H), 7.73-7.63 (m, 3H), 6.88 (s, 2H), 5.83 (s, 1H), 5.39 (bs, 1H), 3.93 (s, 3H), 3.50 (q, J=6.6 Hz, 2H), 2.81 (t, J=6.6 Hz, 2H), 2.24 (s, 3H), 1.86 (s, 3H). MS m/z 485 (M+1).

Sources & evidence

ORD record
ord-35c2284e0d7f4722a1ba7a4a0b466d1e
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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