Isobutylene oxide → 2-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol

HRID 1947840Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (58.74 mg, 0.002448 mol) was added to solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (500.0 mg, 0.002577 mol) in DMF (5 mL) at room temperature. After gas evolution ceased, 2,2-dimethyl-oxirane, (0.46 mL, 0.0052 mol) was added. The mixture was heated to 100° C. for 1 hour. The material was extracted with EtOAc, and washed with water (3×). The organic layer was concentrated in vacuo to afford the title compound as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ=1.04 (s, 6H), 1.25 (s, 12H), 4.03 (s, 2H), 4.68 (s, 1H), 7.56 (s, 1H), 7.84 (s, 1H).

Workup

extractionThe material was extracted with EtOAc
washwashed with water (3×)
concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record: ord-0d098a6851eb41e0b29ea882e93bec15
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399433B2

Reaction notes

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