Sodium Carbonate → HCID 9968772, compound

HRID 586322Notes

Reaction equation

HRID 586322 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.Br[C:24]1[N:28]2[N:29]=[CH:30][C:31]([C:33]([F:36])([F:35])[F:34])=[N:32][C:27]2=[N:26][CH:25]=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:24]2[N:28]3[N:29]=[CH:30][C:31]([C:33]([F:34])([F:35])[F:36])=[N:32][C:27]3=[N:26][CH:25]=2)=[CH:4][C:3]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridineHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazine

Product 1

HCID 9968772HCID 9968772, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-[2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine (151 mg, 0.51 mmol) was coupled to 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.09 g, 0.34 mmol) as described in Example 37, step e, using 2 M Na2CO3 (0.51 ml) and tetrakis(triphenylphosphine)palladium(0) (0.019 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 (54 mg, 45%): 1H NMR (400 MHz, CDCl3) δ 7.38-7.47 (2H, m), 7.94-7.97 (1H, m), 8.08-8.12 (1H, m), 8.24 (1H, dd, J 7.0, 2.3 Hz), 8.62 (1H, s), 8.69 (1H, dd, J 4.8, 1.6 Hz), 8.82 (1H, s), 8.88 (1H, s); MS (ES+) m/z 359, 360.

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-209209350fe041458d5b1639c5878121
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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