tert-Butylhydrazine monohydrochloride → 1-tert-butyl-3-(4-nitrophenyl)-1H-pyrazole

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14](B3OC(C)(C)C(C)(C)O3)=[CH:13]N(CC(OC(C)(C)C)=O)N=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[C:33]([NH:37][NH2:38])([CH3:36])([CH3:35])[CH3:34]>>[CH3:34][C:33]([N:37]1[CH:13]=[CH:14][C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:38]1)([CH3:36])[CH3:35]

Participants

Reactant 2

HCID 81889tert-Butylhydrazine monohydrochloride

HCID 866173901,1-dimethylethyl [3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetate

Product 1

HCID 534855281-tert-butyl-3-(4-nitrophenyl)-1H-pyrazole

Procedure

Following the procedure described for Intermediate 1 with t-butylhydrazine hydrochloride, provided the title compound as the minor isomer. ESMS (M-C(CH3)3+2H): 190.0; HNMR (400 MHz, d6-DMSO) δ 8.20 (d, 2H), 7.86 (d, 2H), 7.7 (d, 1H), 6.55 (d, 1H), 1.25 (s, 9H)

Sources & evidence

ORD record: ord-5b6cb64c9e6946b3b3a6c66e82f7b607
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419988B2

Reaction notes

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