Potassium Carbonate → HCID 59753956, compound

HRID 750879Notes

Reaction equation

HRID 750879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[O:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9](S(C(F)(F)F)(=O)=O)=[C:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:39][C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[O:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9]([C:43]2[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=2)=[C:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86601403HCID 86601403, compound

Product 1

HCID 59753956HCID 59753956, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
82.5 °C

Procedure

To a 5 mL round bottom flask fitted with a stir bar and septum was added 2-(3,4-difluorophenoxy)-4-methoxy-5-trifluoromethansulfonyl-6-[2 4-dichlorophenyl]pyrimidine (85 mg, 0.16 mmol) as described in Reference Example 17, anhydrous potassium carbonate (66 mg, 0.48 mmol) and 4-fluorobenzeneboronic acid (44 mg, 0.32 mmol) in 1 mL 80/20 toluene/ethanol. The mixture was degassed under nitrogen with three freeze-thaw cycles and tetrakis(triphenylphosphine) palladium (27 mg, 0.024 mmol) was added to the reaction mixture and the mixture was heated between 75-90° C. for 4 h. The solvent was removed under reduced pressure and the residue flash chromatographed with 95/5 hexane/ethyl acetate to recover the desired product. HPLC/MS: m/e=477 (M+−1); Rt=4.54 min. 1H-NMR 500 MHz (CDCl3): δ 3.97 (s, 3H), 6.96 (m, 2H), 7.02-7.20 (m, 7H), 7.33 (d, J=2 Hz, 1H).

Workup

  1. customTo a 5 mL round bottom flask fitted with a stir bar
  2. additionwas added to the reaction mixture
  3. customThe solvent was removed under reduced pressure
  4. customthe residue flash chromatographed with 95/5 hexane/ethyl acetate
  5. customto recover the desired product

Sources & evidence

ORD record
ord-5bac8b8cdf764437bc7192c3ac14e558
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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