Sodium hydride → HCID 67253006, compound

HRID 1024379Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8]1)(=O)=O.[CH3:14][C:15]1([CH3:27])[C:19]([CH3:21])([CH3:20])[O:18][B:17]([C:22]2[CH:23]=[N:24][NH:25][CH:26]=2)[O:16]1.[H-].[Na+]>CN(C)C=O>[CH3:13][C:9]1([CH3:12])[O:8][C@@H:7]([CH2:6][N:25]2[CH:26]=[C:22]([B:17]3[O:16][C:15]([CH3:27])([CH3:14])[C:19]([CH3:21])([CH3:20])[O:18]3)[CH:23]=[N:24]2)[CH2:11][O:10]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (1.08, 5.15 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 g, 5.15 mmol) and NaH (262 mg, 10.9 mmol) in N,N-dimethylformamide (25 mL) was heated at 90° C. for 3 hours, then allowed to cool to room temperature., quenched with water and extracted with ethyl acetate (3×). The combined organics were washed with brine, concentrated and the residue was purified by chromatography on an Analogix® Intelliflash™ purification system using a SF25-25 g column at a flow rate of 80 mL/minute, eluting with 0% to 30% ethyl acetate:hexanes over 30 minutes to give the title compound.

Workup

temperatureto cool to room temperature
custom, quenched with water
extractionextracted with ethyl acetate (3×)
washThe combined organics were washed with brine
concentrationconcentrated
customthe residue was purified by chromatography on an Analogix® Intelliflash™ purification system
washeluting with 0% to 30% ethyl acetate

Sources & evidence

ORD record: ord-b34579cb2ca64d8b90d037dcea3a44d3
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722890B2

Reaction notes

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