Sodium Carbonate → Imidazo[5,1-f][1,2,4]triazin-4-amine, N,7-dimethyl-5-[1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]-

HRID 1498051Notes

Reaction equation

HRID 1498051 reaction equation
Br[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH3:19])[N:11]2[C:16]=1[C:15]([NH:17][CH3:18])=[N:14][CH:13]=[N:12]2.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH3:18][NH:17][C:15]1[C:16]2=[C:8]([C:3]3[CH:4]=[N:5][N:6]([CH3:7])[C:2]=3[C:25]3[CH:26]=[CH:27][C:22]([C:21]([F:32])([F:31])[F:20])=[CH:23][CH:24]=3)[N:9]=[C:10]([CH3:19])[N:11]2[N:12]=[CH:13][N:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 68181989HCID 68181989, compound

Product 1

HCID 60163378Imidazo[5,1-f][1,2,4]triazin-4-amine, N,7-dimethyl-5-[1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]-

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

5-(5-Bromo-1-methyl-1H-pyrazol-4-yl)-N,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-amine (500 mg, 1.55 mmol), [4-(trifluoromethyl)phenyl]boronic acid (590 mg, 3.11 mmol), sodium carbonate (329 mg, 3.10 mmol), tetrakis(triphenylphosphine)palladium(0) (179 mg, 0.155 mmol) and ethanol (10 mL) were combined in a microwave vessel. The reaction was subjected to microwave irradiation at 130° C. for 45 minutes at 200 W. The reaction was dried over sodium sulfate, filtered and concentrated in vacuo. Purification via silica gel chromatography (Eluant: 20% tetrahydrofuran in dichloromethane) provided the product as a light yellow solid. Yield: 423 mg, 1.13 mmol, 73%. LCMS m/z 388.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.62 (s, 3H), 2.99 (d, J=4.9 Hz, 3H), 3.96 (s, 3H), 5.46-5.53 (m, 1H), 7.60 (br AB quartet, JAB=8 Hz, ΔvAB=48 Hz, 4H), 7.73 (s, 1H), 7.90 (s, 1H).

Workup

  1. customirradiation at 130° C. for 45 minutes at 200 W
  2. dry with materialThe reaction was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography (Eluant: 20% tetrahydrofuran in dichloromethane)

Sources & evidence

ORD record
ord-17a8c24472a2446381a9baf4f066b151
Source dataset
uspto-grants-2015_12
Patent number
US09200000B2

Reaction notes

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