Methyl iodide → 5-Bromo-3-cyclobutyl-1-methyl-1H-indazole

HRID 1423083Notes

Reaction equation

HRID 1423083 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+].[CH3:17]I>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:17])[N:6]=[C:5]2[CH:11]1[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178419332HCID 178419332, compound

Product 1

HCID 581889995-Bromo-3-cyclobutyl-1-methyl-1H-indazoleYield 71%

Procedure

The title compound was prepared by the method outlined for Preparative Example 59 using the 5-bromo-3-cyclobutyl-1H-indazole intermediate (427 mg, 1.70 mmol), NaH (97.5 mg, 2.25 mmol), and methyl iodide (294 mg, 2.06 mmol) to afford titled compound as a colorless oil (317 mg, 71%). 1H NMR (CDCl3) 7.82 (s, 1H), 7.41 (d, J=8.8, 1H), 7.21 (d, J=8.8, 1H), 3.90 (s, 3H), 3.88 (pent, J=9.2, 1H), 2.51-2.43 (m, 4H), 2.18-2.13 (m, 1H), 2.01 (m, 1H). LC/MS (Method B) 4.05 min, [M+1]+ 265/267.

Workup

  1. customThe title compound was prepared by the method

Sources & evidence

ORD record
ord-59fd3f4af4e5448b809581d757903ce9
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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