Potassium Carbonate → HCID 67125435, compound

HRID 1470717Notes

Reaction equation

HRID 1470717 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH:24]=[C:25]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[CH:4][CH:3]=2)[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 66611344N-(1-(4-Iodophenyl)propan-2-YL)acetamide

Product 1

HCID 67125435HCID 67125435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under inert gas atmosphere 303 mg (1.00 mmol) N-[2-(4-iodo-phenyl)-1-methyl-ethyl]-acetamide (III.2) are added to a mixture of 309 mg (1.00 mmol) 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester, 49 mg (0.060 mmol) PdCl2(dppf)xCH2Cl2 and 415 mg (3.00 mol) K2CO3 in 5 mL DMF. The mixture is stirred for 48 h at rt. After that time, the solvent is evaporated, the residue taken up in ethyl acetate and washed with water. After drying over sodium sulphate, the solvent is removed in vacuo and the residue is purified by column chromatography (silica gel; ethyl acetate) to yield the desired product.

Workup

  1. customAfter that time, the solvent is evaporated
  2. washwashed with water
  3. dry with materialAfter drying over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customthe residue is purified by column chromatography (silica gel; ethyl acetate)

Sources & evidence

ORD record
ord-a5cb96d29a8c418591c163b2411f6302
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

Loading…