Sodium Carbonate → HCID 10133067, compound

HRID 586332Notes

Reaction equation

HRID 586332 reaction equation
CC1(C)COB([C:8]2[CH:9]=[C:10]([C:14]3[N:18]4[N:19]=[CH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[N:22][C:17]4=[N:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)OC1.Br[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][N:30]=1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:8]2[CH:9]=[C:10]([C:14]3[N:18]4[N:19]=[CH:20][C:21]([C:23]([F:24])([F:26])[F:25])=[N:22][C:17]4=[N:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)=[N:30][CH:31]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 22329516HCID 22329516, compound

Product 1

HCID 10133067HCID 10133067, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

7-[3-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.2 g, 0.53 mmol) was added to 1,2-dimethoxyethane (2 ml), 2-bromo-5-fluoropyridine (94 mg, 0.53 mmol) and 2 N Na2CO3 (0.53 ml). The mixture was degassed with a stream of nitrogen for 10 min before tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.027 mmol) was added and the mixture heated at 80° C. for 6 h. The mixture was cooled to ambient temperature before partitioning between water (15 ml) and ethyl acetate (15 ml). The organic extracts were then washed with NaOH (15 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography (silica gel, 3% MeOH/CH2Cl2) then triturated with diethyl ether to give 53 mg (28%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.51-7.56 (1H, m), 7.67 (1H, t, J 7.7 Hz), 7.83 (1H, dd, J 9.2, 4.1 Hz), 8.03 (1H, dq, J 7.7, 1.0 Hz), 8.14 (1H, dq, J 7.7, 1.0 Hz), 8.60 (1H, d, J 3.1 Hz), 8.70 (1H, s), 8.72 (1H, t, J 1.6 Hz), 8.84 (1H, s); MS (ES+) m/z 360 [M+H]+.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled to ambient temperature
  3. custombefore partitioning between water (15 ml) and ethyl acetate (15 ml)
  4. washThe organic extracts were then washed with NaOH (15 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography (silica gel, 3% MeOH/CH2Cl2)
  8. customthen triturated with diethyl ether

Sources & evidence

ORD record
ord-abdc9a0809144cfa82f93b2df3682e16
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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