Sodium Carbonate → HCID 10268440, compound

HRID 586309Notes

Reaction equation

HRID 586309 reaction equation
CC1(C)COB([C:8]2[CH:9]=[C:10]([N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)[CH:11]=[CH:12][CH:13]=2)OC1.Br[C:21]1[N:25]2[N:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[N:29][C:24]2=[N:23][CH:22]=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>[N:14]1([C:10]2[CH:9]=[C:8]([C:21]3[N:25]4[N:26]=[CH:27][C:28]([C:30]([F:31])([F:32])[F:33])=[N:29][C:24]4=[N:23][CH:22]=3)[CH:13]=[CH:12][CH:11]=2)[CH:18]=[N:17][CH:16]=[N:15]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 22329518HCID 22329518, compound

Product 1

HCID 10268440HCID 10268440, compoundYield 55%

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 1-[3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-1H-[1,2,4]triazole (192 mg, 0.75 mmol), 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.1 g, 0.375 mmol), 2 M Na2CO3 (0.75 ml) and tetrakis(triphenylphosphine)palladium(0) (0.022 g) in 1,2-dimethoxyethane (2 ml). The crude residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2) and triturated with Et2O to yield the title compound (68 mg, 55%): 1H NMR (360 MHz, CDCl3) δ 7.72 (1H, t, J 7.8 Hz), 7.76-7.80 (1H, m), 8.09-8.13 (1H, dt, J 7.8, 1.3 Hz), 8.17 (1H, s), 8.57 (1H, t, J 1.9 Hz), 8.67 (1H, s), 8.71 (1H, s), 8.87 (1H, s); MS (ES+) m/z 332 [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-b35f8e502955433698e007c690d66243
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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