3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → HCID 58464781, compound

HRID 2089361Notes

Reaction equation

HRID 2089361 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[CH2:16][CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH2:13][CH2:12]1>>[O:11]1[CH2:12][CH:13]=[C:14]([C:2]2[N:6]([CH3:7])[N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazole

Product 1

HCID 58464781HCID 58464781, compoundYield 65%

Procedure

Following Example 231, reaction of 5-chloro-1-methyl-4-nitro-1H-pyrazole and 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester gave 5-(3,6-dihydro-2H-pyran-4-yl)-1-methyl-4-nitro-1H-pyrazole (167 mg, 65%). 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 5.99-5.94 (m, 1H), 4.37 (q, J=2.8 Hz, 2H), 3.99 (t, J=5.3 Hz, 2H), 3.84 (s, 3H), 2.40-2.35 (m, 2H)

Sources & evidence

ORD record
ord-9d0c22e0179c48d890ef5c2c9581a185
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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