Sodium Carbonate → HCID 9969811, compound

HRID 586327Notes

Reaction equation

HRID 586327 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1.Br[C:19]1[N:23]2[N:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[N:27][C:22]2=[N:21][CH:20]=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:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2[N:23]3[N:24]=[CH:25][C:26]([C:28]([F:29])([F:30])[F:31])=[N:27][C:22]3=[N:21][CH:20]=2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 22329529HCID 22329529, compound

Product 1

HCID 9969811HCID 9969811, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Fluoro-3-(5-fluoropyridin-2-yl)phenylboronic acid (61 mg, 0.25 mmol) was coupled to 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.046 g, 0.17 mmol) as described in Example 37, step e, using 2 M Na2CO3 (0.26 ml) and tetrakis(triphenylphosphine)palladium(0) (0.010 g) in 1,2-dimethoxyethane (2 ml). The crude residue was purified by flash chromatography (silica gel, 2.5% MeOH/CH2Cl2) and triturated with Et2O to yield the title compound (23 mg, 35%): 1H NMR (400 MHz, CDCl3) δ 7.39 (1H, dd, J 8.8, 10.8 Hz), 7.51-7.56 (1H, m), 8.89-7.94 (1H, m), 8.14-8.17 (1H, m), 8.63 (1H, d, J 2.7 Hz), 8.66 (1H, s), 8.74 (1H, dd, J 7.4, 2.3 Hz), 8.83 (1H, s); MS (ES+) m/z 378 [M+H]+.

Workup

  1. customThe crude residue was purified by flash chromatography (silica gel, 2.5% MeOH/CH2Cl2)
  2. customtriturated with Et2O

Sources & evidence

ORD record
ord-8bc12f0548704f0db19bbc76f419505d
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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