Potassium Carbonate → HCID 58775905, compound

HRID 1715337Notes

Reaction equation

HRID 1715337 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH3:22])=[CH:16][CH:15]=1)=[O:12].B(O)(O)[C:33]1[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=1>C1(C)C=CC=CC=1.C(O)C.O>[CH:23]1([N:21]([CH2:20][C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:11]([C:10]3[CH:9]=[C:8]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)[CH:31]=[CH:30][CH:29]=3)=[O:12])=[CH:15][CH:16]=2)[CH3:22])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 58775917HCID 58775917, compound

Product 1

HCID 58775905HCID 58775905, compound

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

K2CO3 (0.2 mmol, 0.03 g) and a Pd(dppf)2 catalyst:DCM complex (1:1) (0.03 mmol, 0.02 g) was added to a mixture of 3-bromo-N-{4-[(cyclohexyl-methyl-amino)-methyl]-phenyl}-benzamide Compound 10f (0.1 mmol, 0.04 g) and p-tolylboronic acid Compound 11a (0.12 mmol, 0.02 g) in a mixed solution of toluene/ethanol/water (7 mL/1 mL/1 mL). The resulting suspension was heated to reflux for 5 hrs, concentrated and purified with preparative TLC (10% MeOH/2% Et3N/88% EtOAc) to yield 4′-methyl-biphenyl-3-carboxylic acid {4-[(cyclohexyl-methyl-amino)-methyl]-phenyl}amide Compound 11b (0.02 g, 48%). MS m/e 413 (M+1).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 5 hrs
  3. concentrationconcentrated
  4. custompurified with preparative TLC (10% MeOH/2% Et3N/88% EtOAc)

Sources & evidence

ORD record
ord-7fb96d2d10fe46ad84fe2c6ba8294519
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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