Potassium Carbonate → HCID 66616016, compound

HRID 2367063Notes

Reaction equation

HRID 2367063 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:27])[C:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2Br)([CH3:18])[CH3:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(B(O)O)C=CC=CC=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:20]3[C:19](=[CH:24][C:23]([F:25])=[CH:22][CH:21]=3)[C:16]([CH3:18])([CH3:17])[C:15]2=[O:27])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66616147HCID 66616147, compound

Product 1

HCID 66616016HCID 66616016, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

A mixture of N-(1-benzylpiperidin-4-yl)-2-(2-bromo-5-fluorophenyl)-2-methylpropanamide (275 mg, 0.635 mmol, EXAMPLE 44, Step 2), palladium acetate (14 mg, 0.063 mmol), phenyl boronic acid (15 mg, 0.13 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (30 mg, 0.063 mmol), potassium carbonate (220 mg, 1.6 mmol) and t-butyl alcohol (15 mL) was refluxed under nitrogen atmosphere for 14 h. The mixture was cooled to room temperature, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (8-66% ethyl acetate in hexane) to give the title compound (171 mg, 76%).

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 14 h
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (8-66% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-566c8f64f5ea40abbdd1c6e6c057bd3e
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

Loading…