2-Bromo-4-fluoroanisole → HCID 11475569, compound

HRID 2374949Notes

Reaction equation

HRID 2374949 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:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[O:30][CH3:31].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]>[F:29][C:27]1[CH:26]=[CH:25][C:24]([O:30][CH3:31])=[C:23]([NH:11][C:7]2[N:8]=[CH:9][C:10]3=[C:2]([CH3:1])[N:3]=[C:4]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=4)[N:5]3[N:6]=2)[CH:28]=1

Participants

7

Reactant 4

HCID 1362922-Bromo-4-fluoroanisoleHCID 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 11475569HCID 11475569, compoundYield 29.3%

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-bromo-4-fluoro-1-methoxybenzene (0.017 g, 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 N-(5-fluoro-2-methoxyphenyl)-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (0.011 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.17 (s, 1H), 8.83-8.79 (m, 1H), 8.76 (s, 1H), 8.16 (dd, J=10.9, 3.0 Hz, 1H), 7.87-7.74 (m, 3H), 7.09-7.04 (m, 1H), 6.83-6.76 (m, 1H), 3.98 (s, 3H), 2.59 (s, 3H). MS m/z 418 (M+1).

Sources & evidence

ORD record
ord-bdd86f3db67643a783b64bb43149b647
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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