Sodium Carbonate → HCID 10268869, compound

HRID 586307Notes

Reaction equation

HRID 586307 reaction equation
CC1(C)COB([C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:10]2[CH:9]=[C:8]([C:22]3[N:26]4[N:27]=[CH:28][C:29]([C:31]([F:32])([F:33])[F:34])=[N:30][C:25]4=[N:24][CH:23]=3)[CH:13]=[CH:12][CH:11]=2)[CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 223295173-[3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]pyridine

Product 1

HCID 10268869HCID 10268869, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 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]pyridine (150 mg, 0.56 mmol), 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.1 g, 0.375 mmol), 2 M Na2CO3 (0.56 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) to yield the title compound (56 mg, 44%): 1H NMR (400 MHz, CDCl3) δ 7.42-7.45 (1H, m), 7.68-7.70 (2H, m), 7.95-7.98 (1H, m), 8.09-8.12 (1H, m), 8.34-8.35 (1H, m), 8.67 (1H, dd, J 4.7, 1.8 Hz), 8.68 (1H, s), 8.84 (1H, s), 8.93 (1H, dd, J 2.5, 0.8 Hz); MS (ES+) m/z 342 [M+H]+.

Workup

  1. customThe crude residue was purified by flash chromatography (silica gel, 5% MeOH(CH2Cl2)

Sources & evidence

ORD record
ord-34445c5d5d9e4b0b95bfdadd96bd8bbd
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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