Sodium Carbonate → HCID 9902886, compound

HRID 586318Notes

Reaction equation

HRID 586318 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([F:19])=[C:12]([N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)[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>[F:19][C:11]1[CH:10]=[CH:9][C:8]([C:22]2[N:26]3[N:27]=[CH:28][C:29]([C:31]([F:32])([F:33])[F:34])=[N:30][C:25]3=[N:24][CH:23]=2)=[CH:13][C:12]=1[N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 223294911-[5-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-2-fluorophenyl]-1H-imidazole

Product 1

HCID 9902886HCID 9902886, compoundYield 13.2%

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-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-1H-imidazole (344 mg, 1.67 mmol), 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.446 g, 1.67 mmol), 2 M Na2CO3 (1.67 ml) and tetrakis(triphenylphosphine)palladium(0) (0.096 g) in 1,2-dimethoxyethane (6 ml). The crude residue was purified by flash chromatography (silica gel, 3% MeOH(CH2Cl2) and triturated with Et2O to yield the title compound (77 mg, 13%): 1H NMR (360 MHz, CDCl3) δ 7.29 (1H, s), 7.35 (1H, d, J 1.4 Hz), 7.50 (1H, t, J 9.1 Hz), 7.92 (1H, s), 8.04-8.08 (1H, m), 8.30 (1H, dd, J 7.0, 2.1 Hz), 8.64 (1H, s), 8.84 (1H, s); MS (ES+) m/z 349 [M+H]+.

Workup

  1. customThe crude residue was purified by flash chromatography (silica gel, 3% MeOH(CH2Cl2)
  2. customtriturated with Et2O

Sources & evidence

ORD record
ord-b6f6c59ea0d6404d96bd58601ff99d7b
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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