Sodium Carbonate → HCID 9967813, compound

HRID 586330Notes

Reaction equation

HRID 586330 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(OCC)(=O)C.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>[N:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:3]=[C:4]([C:8]3[N:12]4[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]4=[N:10][CH:9]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 22329530HCID 22329530, compound

Product 1

HCID 9967813HCID 9967813, compoundYield 44.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 7-(3-bromophenyl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (21 mg, 0.06 mmol), 4-pyridylboronic acid (11 mg, 0.09 mmol) and 2 M Na2CO3 (0.09 ml) in 1,2-dimethoxyethane (1.5 ml) was degassed with a stream of nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (4 mg, 0.003 mmol) was added and the mixture was stirred under nitrogen at 65° C. for 12 h. After allowing to cool to room temperature, the mixture was diluted with ethyl acetate and partitioned between water (20 ml) and ethyl acetate (30 ml). The organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2) and triturated with diethyl ether to give 9.2 mg (44%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.58 (2H, m), 7.70 (1H, t, J 7.3 Hz), 7.74-7.77 (1H, m), 8.13 (1H, dt, J 7.3, 1.6 Hz), 8.39 (1H, t, J 1.6 Hz), 8.68 (1H, s), 8.72 (2H, m), 8.83 (1H, s); MS (ES+) m/z 342 [M+H]+.

Workup

  1. customwas degassed with a stream of nitrogen for 10 min
  2. temperatureto cool to room temperature
  3. custompartitioned between water (20 ml) and ethyl acetate (30 ml)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2)
  7. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-7eca0fb3e9ef41d389e006bc0c810c9d
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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