Sodium Carbonate → 4-[(4-ethoxycarbonylaminophenyl)-(3-fluorophenyl)-methyl]-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 2120904Notes

Reaction equation

HRID 2120904 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14](Br)[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)[C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([F:28])[CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 692435694-[Bromo-(4-ethoxycarbonylamino-phenyl)-methyl]-piperidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 536899394-[(4-ethoxycarbonylaminophenyl)-(3-fluorophenyl)-methyl]-piperidine-1-carboxylic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of compound 88 (0.30 g, 0.625 mmoles) and tetrakis(triphenyl phosphine), palladium(0) (50 mg) in toluene (degassed, 5 mL) was added 3-fluorophenyl boronic acid (0.182 g, 1.3 mmoles) in ethanol (degassed, 5 mL) followed by 0.75 mL 2M Na2CO3 (aq) (1.5 mmoles). The reaction was allowed to proceed at 80° C. for 3 hrs under argon. The reaction was diluted with water and diethyl ether and vortexed. The organic phase was isolated and evaporated to give a crude product. The crude product was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the product (compound 92) as a white powder (0.166 g, 58% yield).

Workup

  1. customThe organic phase was isolated
  2. customevaporated
  3. customto give a crude product
  4. customThe crude product was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-24158e1f34ef4307bb01452d61658089
Source dataset
uspto-grants-2004_02
Patent number
US06693117B2

Reaction notes

Loading…