2-Bromopropane → 5-Bromo-3-cyclobutyl-1-isopropyl-1H-indazole

HRID 1423084Notes

Reaction equation

HRID 1423084 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]1[CH2:14][CH2:13][CH2:12]1.[H-].[Na+].Br[CH:18]([CH3:20])[CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:18]([CH3:20])[CH3:19])[N:6]=[C:5]2[CH:11]1[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 178419332HCID 178419332, compound

Product 1

HCID 581890485-Bromo-3-cyclobutyl-1-isopropyl-1H-indazoleYield 70%

Procedure

The title compound was prepared by the method outlined for Preparative Example 59 using 5-bromo-3-cyclobutyl-1H-indazole intermediate (1.05 g, 4.16 mmol), NaH (211 mg, 5.26 mmol), and 2-bromopropane (667 mg, 5.42 mmol) to afford titled compound as a light yellow oil (850 mg, 70%). 1H NMR (CDCl3) 7.86 (s, 1H), 7.37 (d, J=8.8, 1H), 7.27 (d, J=8.8, 1H), 4.75 (m, 1H), 3.88 (pent, J=8.4, 1H), 2.55-2.43 (m, 4H), 2.15-2.05 (m, 1H), 2.01 (m, 1H), 1.57 (d, J=6.8, 6H). LC/MS (Method B) 4.72 min, [M+1]+ 293/295.

Workup

  1. customThe title compound was prepared by the method

Sources & evidence

ORD record
ord-106950b18d454a749ca8a845325bcfd5
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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