4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → tert-butyl (2,2-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propyl)carbamate

HRID 873610Notes

Reaction equation

HRID 873610 reaction equation
O[CH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[CH3:15][C:16]1([CH3:28])[C:20]([CH3:22])([CH3:21])[O:19][B:18]([C:23]2[CH:24]=[N:25][NH:26][CH:27]=2)[O:17]1.C(P(CCCC)(CCCC)=CC#N)CCC>C1(C)C=CC=CC=1>[CH3:13][C:3]([CH3:14])([CH2:2][N:26]1[CH:27]=[C:23]([B:18]2[O:17][C:16]([CH3:28])([CH3:15])[C:20]([CH3:22])([CH3:21])[O:19]2)[CH:24]=[N:25]1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 4622928CyanomethylenetributylphosphoraneHCID 21263232tert-butyl N-(3-hydroxy-2,2-dimethylpropyl)carbamate

Product 1

HCID 86702127tert-butyl (2,2-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propyl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl (3-hydroxy-2,2-dimethylpropyl)carbamate (1.000 g, 4.92 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.145 g, 5.90 mmol) and 2-(tributylphosphoranylidene)acetonitrile (1.425 g, 5.90 mmol) were stirred together in toluene (20 ml) at 90° C. overnight. The reaction mixture was concentrated and purified by normal phase chromatography to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-3f737615f2594429ad2f2b155abdc2af
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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