Potassium Fluoride → HCID 44193859, compound

HRID 2076125Notes

Reaction equation

HRID 2076125 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH2:17][CH2:16][CH2:15][CH:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[N:13]=2)=[CH:4][C:3]=1[O:24][CH3:25].[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.[F-].[K+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][O:24][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[S:10][C:11]3[CH2:17][CH2:16][CH2:15][CH:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[N:13]=2)[CH:6]=[CH:7][C:2]=1[C:30]1[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86632611HCID 86632611, compound

Product 1

HCID 44193859HCID 44193859, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

In a microwave vial a mixture of (4-bromo-3-methoxy-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine (120 mg, 0.289 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (185 mg, 0.88 mmol), palladium (II) acetate (6 mg 0.027 mmol) and potassium fluoride (51 mg, 0.867 mmol) in 6 ml methanol was purged with nitrogen. The vial was sealed and the mixture was irradiated for ½ h at 140° C. in a microwave oven. The reaction mixture was filtered and the filtrate was concentrated, the residue was dissolved in dichloromethane, washed three times with water, dried and evaporated in vacuo. Column chromatography (12 g silica, dichloromethane+1.8% methanol v/v) afforded the title compound (19 mg, 16%) as a light brown wax. MS ISP (m/e): 417.1 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.79 (s, 1H), 7.75 (s, 1H), 7.38 (d, 1H), 7.22 (m, 6H), 6.97 (s, broad, 1H), 6.65 (dd, 1H), 4.05 (s broad, 1H), 3.92 (s, 3H), 3.68 (s, 3H), 2.75 (m broad, 2H), 2.20 (m broad, 1H), 1.88 (m broad, 3H).

Workup

  1. customwas purged with nitrogen
  2. customThe vial was sealed
  3. customthe mixture was irradiated for ½ h at 140° C. in a microwave oven
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. dissolutionthe residue was dissolved in dichloromethane
  7. washwashed three times with water
  8. customdried
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3304eb6d5e814bb89d4d19142ee0b146
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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