Potassium Carbonate → HCID 66916938, compound

HRID 2075128Notes

Reaction equation

HRID 2075128 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C.O>[ClH:16].[Cl:16][C:17]1[CH:22]=[C:21]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[O:9])=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 13180300(4-Bromophenyl)(piperidin-4-yl)methanone

Product 1

HCID 66916938HCID 66916938, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A round bottom flask was charged with (4-bromophenyl)(piperidine-4-yl)methanone (4.00 g, 14.9 mmol), 3-chlorophenyl boronic acid (3.26 g, 20.9 mmol, 1.4 eq), and Fibrecat 1029® (0.70 g, 0.448 mmol, 0.03 eq, Johnson Matthey). These solids were suspended in isopropanol (68 ml) and allowed to stir for five minutes. To this stirring solution was added potassium carbonate (6.18 g, 44.8 mmol, 3 eq.) dissolved in H2O (12 ml). The resulting solution was heated to 80° C. for 16 hours, at which time the reaction was deemed complete by LC/MS. The reaction mixture was filtered through a small bed of Celite® and the filtrate was concentrated to dryness. The resulting solids were dissolved in isopropyl acetate (100 ml) and washed with water (3×50 ml). The organics were cooled to 0° C., and to this stirring mixture was added slowly 6N HCl until solids crashed out of solution. The solids were filtered and dried for 16 hours at 50° C. in a vacuum oven to afford 2.89 g of compound 2 (72%) in >98% HPLC purity. MH+=300, 302 (about 3:1). Palladium: 4 ppm

Workup

  1. filtrationThe reaction mixture was filtered through a small bed of Celite®
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe resulting solids were dissolved in isopropyl acetate (100 ml)
  4. washwashed with water (3×50 ml)
  5. temperatureThe organics were cooled to 0° C.
  6. additionto this stirring mixture was added slowly 6N HCl until solids
  7. filtrationThe solids were filtered
  8. customdried for 16 hours at 50° C. in a vacuum oven

Sources & evidence

ORD record
ord-0719411dd49547298d2b8f029bbb0461
Source dataset
uspto-grants-2011_04
Patent number
US07919618B2

Reaction notes

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