Sodium hydride → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-1H-pyrazole

HRID 588646Notes

Reaction equation

Br[CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:13][C:14]1([CH3:26])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:22]=[N:23][NH:24][CH:25]=2)[O:15]1.[H-].[Na+]>CN(C)C=O>[CH3:13][C:14]1([CH3:26])[C:18]([CH3:19])([CH3:20])[O:17][B:16]([C:21]2[CH:25]=[N:24][N:23]([CH2:2][C:3]34[CH2:12][CH:7]5[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]5)[CH2:4]3)[CH2:10]4)[CH:22]=2)[O:15]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1-(bromomethyl)adamantane (0.458 g) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.377 g) in N,N-dimethylformamide (5 mL) was cooled to 0° C. To this solution was added 60% sodium hydride (0.096 g). The solution was heated at 70° C. overnight. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 25% ethyl acetate in hexanes to provide the title compound.

Workup

temperatureThe solution was heated at 70° C. overnight
customThe reaction mixture was partitioned between water and ethyl acetate
extractionThe aqueous layer was extracted with additional ethyl acetate twice
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash column chromatography on silica gel eluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-9cc8de4df8764f2d9025e7d5839024a4
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227963B2

Reaction notes

Loading…