Sodium Carbonate → HCID 66682602, compound

HRID 530310Notes

Reaction equation

HRID 530310 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:29])[C:15]([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24](Br)[CH:23]=3)[N:19]=[CH:18]2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)(=[O:32])[NH2:31].C(=O)([O-])[O-].[Na+].[Na+].ClCCl.CO>C(O)CC.O.ClCCl.C(O)(C)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:29])[C:15]([N:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[C:24]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]([C:30](=[O:32])[NH2:31])[CH:38]=4)[CH:25]=[CH:26][CH:27]=3)[N:19]=[CH:18]2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 21226129Dichloromethane methanolHCID 66682853HCID 66682853, compound

Product 1

HCID 66682602HCID 66682602, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 10311-PropanolSolventHCID 21966342Isopropanol methylene chlorideSolvent

Conditions

Temperature
90 °C

Procedure

Tetrakis(triphenylphosphine)palladium complex (0.076 g, 0.066 mmol) was added to a stirred dispersion of N-(1-benzylpiperidin-4-yl)-4-(3-bromophenyl)-N-methyl-1H-imidazole-1-carboxamide (0.600 g, 1.323 mmol), 3-carbamoylphenylboronic acid (0.229 g, 1.390 mmol) and a 2 M solution of sodium carbonate (0.794 mL, 1.588 mmol) in a mixture of 1-propanol (5 mL) and water (1 mL) at room temperature. The reaction mixture was allowed to stir at 90° C. for 1 h. Water was added and the organic layer was diluted with a mixture of dichloromethane/isopropanol (7:3). The organic layer was separated, dried (MgSO4), filtered and evaporated to give an orange oil. Column chromatography (silica, dichloromethane/methanol 5%) gave the product as an orange oil. The oil was triturated with a mixture of petroleum ether/ethyl acetate/ether to give the product as a beige solid (123 mg, 17%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give an orange oil

Sources & evidence

ORD record
ord-980a93fc166647c38094fb20848915aa
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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