Sodium Carbonate → HCID 10269021, compound

HRID 586302Notes

Reaction equation

HRID 586302 reaction equation
CC1(C)COB([C:8]2[CH:9]=[C:10]([C:14]3[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=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+]>C1COCC1.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>[CH3:19][N:16]1[CH:17]=[CH:18][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)=[N:15]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 223295543-[3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-1-methyl-1H-pyrazole

Product 1

HCID 10269021HCID 10269021, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-1-methyl-1H-pyrazole (from above), 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (300 mg, 1.1 mmol) and sodium carbonate (1.7 ml of a 2 N solution, 3.4 ml) in THF (7 ml) was degassed with nitrogen for 15 min. After this time tetrakis(triphenylphosphine)palladium(0) (130 mg, 0.11 mmol) was added and the mixture heated at reflux for 18 h. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (30 ml) and 1 N NaOH (2×30 ml). The organic phase was separated and washed with brine (30 ml), dried (MgSO4) and evaporated. The residue was chromatographed (silica gel, 2.5% MeOH/CH2Cl2) and the fractions containing the desired product were combined and evaporated. The residue was triturated with diethyl ether twice to afford the title compound (140 mg, 36%) as a colourless solid: 1H NMR (400 MHz, CDCl3) δ 3.99 (3H, s), 6.62 (1H, d, J 2.2 Hz), 7.43 (1H, d, J 2.2 Hz), 7.58 (1H, t, J 7.8 Hz), 7.89 (1H, dd, J 7.8, 1.2 Hz), 8.03 (1H, d, J 7.9 Hz), 8.51 (1H, t, J 1.5 Hz), 8.68 (1H, s), 8.80 (1H, s); MS (ES+) m/z 345 [M+H]+.

Workup

  1. customwas degassed with nitrogen for 15 min
  2. temperaturethe mixture heated
  3. temperatureat reflux for 18 h
  4. customThe solvent was evaporated in vacuo
  5. customthe residue partitioned between ethyl acetate (30 ml) and 1 N NaOH (2×30 ml)
  6. customThe organic phase was separated
  7. washwashed with brine (30 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was chromatographed (silica gel, 2.5% MeOH/CH2Cl2)
  11. additionthe fractions containing the desired product
  12. customevaporated
  13. customThe residue was triturated with diethyl ether twice

Sources & evidence

ORD record
ord-3ad1841ecaa04b2f951ce1072a575546
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

Loading…