Sodium Carbonate → HCID 86759821, compound

HRID 586316Notes

Reaction equation

HRID 586316 reaction equation
CC1(C)COB([C:8]2[CH:9]=[C:10]([C:14]3[N:18]=[CH:17][N:16]([CH3:19])[N:15]=3)[CH:11]=[CH:12][CH:13]=2)OC1.Br[C:22]1[N:26]2[N:27]=[CH:28][C:29]([C:31]([F:34])([F:33])[F:32])=[N:30][C:25]2=[N:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:19][N:16]1[CH:17]=[N:18][C:14]([C:10]2[CH:9]=[C:8]([C:28]3[C:29]([C:31]([F:33])([F:34])[F:32])=[N:30][C:25]4[N:26]([CH:22]=[CH:23][N:24]=4)[N:27]=3)[CH:13]=[CH:12][CH:11]=2)=[N:15]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 22329527HCID 22329527, compound

Product 1

HCID 86759821HCID 86759821, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

This reaction was carried out as described in Example 37, step e, using 3-[3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-1-methyl-1H-[1,2,4]triazole (515 mg, 1.9 mmol), 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.461 g, 1.73 mmol), 2 M Na2CO3 (1.9 ml) and tetrakis(triphenylphosphine)palladium(0) (0.1 g) in 1,2-dimethoxyethane (4 ml). The crude residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2) and triturated with Et2O to yield the title compound (346 mg, 58%). 1H NMR (360 MHz, CDCl3) δ 4.02 (3H, s), 7.64 (1H, t, J 7.9 Hz), 8.11 (1H, s), 8.16 (1H, dt, J 8.2, 1.6 Hz), 8.21 (1H, dt, J 8.2, 1.6 Hz), 8.71 (1H, s), 8.81 (1H, t, J 1.4 Hz), 8.84 (1H, s); MS (ES+) m/z 346 [M+H]+.

Workup

  1. customThe crude residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2)
  2. customtriturated with Et2O

Sources & evidence

ORD record
ord-e2462c4bdaaa4d73a8f2f2131a9044fd
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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