Sodium hydride → 1-(Tetrahydrofuran-3-YL)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazole

HRID 500204Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Tetrahydrofuran-3-yl methanesulfonate was dissolved in N,N-dimethylformamide (0.5 mL) and added to a pre-stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (100 mg, 0.52 mmol) and sodium hydride (25 mg, 1.1 mmol) in N,N-dimethylformamide (1 mL). The mixture was heated to 60° C. for 2 d, cooled to RT, and purified by RP-HPLC to afford the desired product. LCMS: (M+H)=265.1.

Workup

temperaturecooled to RT
custompurified by RP-HPLC

Sources & evidence

ORD record: ord-060ef609efa94a31874313afc2e69489
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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