Chloroacetonitrile → (5-Bromo-3-cyclobutyl-1H-indazol-1-yl)acetonitrile

HRID 1423085Notes

Reaction equation

HRID 1423085 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+].Cl[CH2:18][C:19]#[N:20]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:18][C:19]#[N:20])[N:6]=[C:5]2[CH:11]1[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 178419332HCID 178419332, compound

Product 1

HCID 58188977(5-Bromo-3-cyclobutyl-1H-indazol-1-yl)acetonitrileYield 62%

Procedure

The title compound was prepared by the method outlined for Preparative Example 59 using 5-bromo-3-cyclobutyl-1H-indazole intermediate (225 mg, 0.898 mmol), NaH (41 mg, 1.02 mmol), and chloroacetonitrile (78 mg, 1.03 mmol) to afford titled compound as an off-white solid (160 mg, 62%). 1H NMR (DMSO-d6) 7.99 (s, 1H), 7.72 (d, J=8.8, 1H), 7.62 (d, J=8.8, 1H), 5.74 (s, 2H), 3.91 (pent, J=8.8, 1H), 2.38-2.32 (m, 4H), 2.08-2.06 (m, 1H), 1.95 (m, 1H). LC/MS (Method B) 3.99 min, [M+1]+ 290/292].

Workup

  1. customThe title compound was prepared by the method

Sources & evidence

ORD record
ord-fd942f27b7c447838557d327e9899c83
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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