Sodium Carbonate → HCID 178432499, compound

HRID 1371133Notes

Reaction equation

HRID 1371133 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(O)C.C1(C)C=CC=CC=1>[CH3:8][C:6]1[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]2=[C:2]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:19]([F:30])([F:29])[F:18])[CH:25]=2)[N:7]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 178432852HCID 178432852, compound

Product 1

HCID 178432499HCID 178432499, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (50 mg, 0.21 mmol), 3-(trifluoromethyl)phenylboronic acid (Fluka) (55 mg, 0.287 mmol, 1.4 eq), tris(dibenzylideneacetone)dipalladium (0) (Aldrich Chemical Company) (4.7 mg, 0.0051 mmol, 0.025 eq) and triphenylphosphine (Aldrich Chemical Company) (10.8 mg, 0.041 mmol, 0.2 eq) in a mixed solvent (600 μL of toluene, 300 μL of 1.0 M Na2CO3, and 150 μL of ethanol) was heated at reflux under N2 for 19 h. Upon cooling to the room temperature, the reaction mixture was diluted with H2O (20 mL) and extracted with CHCl3 (3×20 mL). The organic phase was dried over Na2SO4, filtered, and concentrated with a rotary evaporator. Mp: 206-208° C. 1H NMR (CDCl3, 400 MHz): δ 8.58 (s, 1), 8.28 (s, 1), 8.18 (d, 1, J=7.6), 7.82 (d, 1, J=7.8), 7.77-7.72 (m, 3), 7.53 (t, 2, J=7.4), 7.46 (t, 1, J=7.4), 6.98(d, 1, J=2.0), 2.89 (s, 3). MS m/z: 354 (M+1), 352 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 19 h
  3. extractionextracted with CHCl3 (3×20 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-75c6a15c51c14c91b5cd75ee3fc7f487
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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