1-Propanol → HCID 66959030, compound

HRID 1984376Notes

Reaction equation

HRID 1984376 reaction equation
Br[C:2]1[C:3]([C:15]#[N:16])=[N:4][N:5]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[CH2:7][CH2:8][CH2:9][CH3:10].[CH3:17][C:18]([CH3:32])([CH3:31])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O)=[O:20].C(O)CC.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:7]([C:6]1[N:5]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:4]=[C:3]([C:15]#[N:16])[C:2]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:19](=[O:20])[C:18]([CH3:31])([CH3:17])[CH3:32])[CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 41935022-(tert-Butylcarbonylamino)phenylboronic acidHCID 66958775HCID 66958775, compound

Product 1

HCID 66959030HCID 66959030, compoundYield 40.4%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

4-Bromo-5-butyl-1-tert-butyl-1H-pyrazole-3-carbonitrile (3.0 g, 10.6 mmol) was treated with triphenylphosphine (0.085 g, 0.32 mmol), 2-[(2,2-dimethylpropanoyl)amino]phenylboronic acid (prepared as described in Part G of Example 23, 2.41 g, 15.8 mmol), 1-propanol (22 mL), palladium (II) acetate (0.024 g, 0.11 mmol), 2 M aqueous sodium carbonate (6.5 mL, 13.0 mmol), and water (4.4 mL) according to the general procedure described in Examples 37-39. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-25% ethyl acetate in hexanes) to yield 1.63 g of N-[2-(5-butyl-1-tert-butyl-3-cyano-1H-pyrazol-4-yl)phenyl]-2,2-dimethylpropanamide as an oil.

Workup

  1. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-35654a75f94a4162b3d4acb653fd91d4
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

Loading…