1-Bromo-4-chlorobutane → 1-(4-bromobutyl)-5-fluoro-3-iodo-1H-indazole

HRID 868865Notes

Reaction equation

HRID 868865 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[I:11].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16]Cl>>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[C:5]([I:11])=[N:6]1

Participants

3

Reactant 2

HCID 813641-Bromo-4-chlorobutaneHCID 178505475HCID 178505475, compound

Product 1

HCID 902165931-(4-bromobutyl)-5-fluoro-3-iodo-1H-indazoleYield 74%

Procedure

The title compound was prepared from 5-fluoro-3-iodo-indazole and 1-bromo-4-chlorobutane in 74% yield according to the general procedure for Preparation 11A. The minor isomer was not isolated or characterized. 1H NMR (400 MHz, CDCl3): δ 1.76-1.80 (2H, m), 2.07-2.11 (2H, m), 3.55 (2H, t, J=6.4 Hz), 4.42 (2H, t, J=6.8 Hz), 7.11 (1H, dd, J=2.0, 8.4 Hz), 7.22 (1H, td, J=2.4, 8.8 Hz), 7.33 (1H, dd, J=4.0, 9.2 Hz).

Workup

  1. customThe minor isomer was not isolated

Sources & evidence

ORD record
ord-c7fe5fb832e940c6882c336407521e1a
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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