Sodium Carbonate → HCID 66599216, compound

HRID 1893410Notes

Reaction equation

HRID 1893410 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[N:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:5]3=[N:4][C:3]=2[C:11]([F:14])([F:13])[F:12])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 66598996HCID 66598996, compound

Product 1

HCID 66599216HCID 66599216, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Bromo-2-(trifluoromethyl)imidazo[1,2-a]pyrazine (I12) (1.330 g, 5 mmol), (4-fluorophenyl)boronic acid (1.049 g, 7.50 mmol), sodium carbonate (2.65 g, 25.00 mmol) and Bis(triphenylphosphine)palladium (II) chloride (0.351 g, 0.500 mmol) were heated at 80° C. for 7 h in water (10 ml) and 1,2-dimethoxyethane (DME) (20 ml). The mixture was passed through a hydromatrix cartridge (Varian, 20 g) and washed through with dichloromethane. The filtrated was concentrated in vacuo to afford a tacky oil. The product was purified by flash chromatography (Isolera, 100 g, 0-100% 2M ammonia in methanol:dichloromethane (1:9)/dichloromethane) to afford product in 2.03 g. The compound was repurified by flash chromatography (Isolera, 100 g, 0-100% ethyl acetate/iso-hexane) to afford product in 1.42 g as beige solid.

Workup

  1. washwashed through with dichloromethane
  2. concentrationThe filtrated was concentrated in vacuo
  3. customto afford a tacky oil
  4. customThe product was purified by flash chromatography (Isolera, 100 g, 0-100% 2M ammonia in methanol:dichloromethane (1:9)/dichloromethane)
  5. customto afford product in 2.03 g
  6. customThe compound was repurified by flash chromatography (Isolera, 100 g, 0-100% ethyl acetate/iso-hexane)
  7. customto afford product in 1.42 g as beige solid

Sources & evidence

ORD record
ord-32fd4b3a7bb9457990a2a76d2b9614bf
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

Loading…