5-Nitroindazole → 1-(Cyclopropylmethyl)-5-nitro-1H-indazole

HRID 2102021Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1>>[CH:15]1([CH2:14][N:9]2[C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[CH:7]=[N:8]2)[CH2:17][CH2:16]1

Participants

Reactant 2

HCID 215015-Nitroindazole

HCID 81503Bromomethylcyclopropane

Product 1

HCID 578002301-(Cyclopropylmethyl)-5-nitro-1H-indazole

Procedure

Synthesized as described in Example 4 using 5-nitro-1H-indazole and (bromomethyl)cyclopropane to afford a mixture of regioisomers. The following data are for the title regioisomer: 1H NMR (400 MHz, CDCl3) δ 8.73 (d, J=2.0 Hz, 1H), 8.26 (dd, J=9.3 and 2 Hz, 1H), 8.20 (s, 1H), 7.48 (d, J=9.3 Hz, 1H), 4.31 (d, J=6.8 Hz, 2H), 1.35 (m, 1H), 0.62 (m, 2H), 0.44 (m, 2H); MS (ES) m/z 218 (M+1).

Workup

customSynthesized
customto afford
additiona mixture of regioisomers

Sources & evidence

ORD record: ord-3c2eb1accc8748a990c28ebc878d36b1
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572820B2

Reaction notes

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