2-(Di-tert-butylphosphino)biphenyl → 3-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)benzenesulfonamide

HRID 2374939Notes

Reaction equation

HRID 2374939 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]([S:29]([NH2:32])(=[O:31])=[O:30])[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]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)=[N:6]2

Participants

7

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27347653-Bromobenzene-1-sulfonamideHCID 23676156Sodium t-butoxideHCID 587120012-Amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin2×

Product 1

HCID 114422543-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)benzenesulfonamideYield 19.8%

Reagents, catalysts & solvents 2

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

Procedure

A mechanical mixture of 5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (Intermediate 45) (0.025 g, 0.09 mmol), 3-bromobenzenesulfonamide (0.02 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) was irradiated with microwave radiation for 1000 seconds at a temperature of 150° C. Filtration of the resultant through celite, followed by concentration and purification by preparative HPLC gave 3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)benzenesulfonamide (0.008 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.19 (s, 1H), 8.98-8.93 (m, 1H), 8.81 (bs, 1H), 8.42-8.37 (m, 1H), 8.10-8.05 (m, 1H), 7.95-7.90(m, 1H), 7.81-7.75 (m, 1H), 7.67-7.50 (m, 2H), 6.63 (bs, 1H), 2.60 (s, 3H). MS m/z 449 (M+1).

Workup

  1. customwas irradiated with microwave radiation for 1000 seconds at a temperature of 150° C
  2. filtrationFiltration of the resultant through celite
  3. concentrationfollowed by concentration and purification by preparative HPLC

Sources & evidence

ORD record
ord-9b30518991504605b96e8ff54ef3ed68
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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