Tert-butyl[(5-chloropentyl)oxy]dimethylsilane → 1-(5-tert-butyldimethylsiloxypentyl)-5-fluoro-3-iodo-1H-indazole

HRID 868866Notes

Reaction equation

HRID 868866 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].Cl[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[O:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][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)[Si:19]([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 13249888Tert-butyl[(5-chloropentyl)oxy]dimethylsilaneHCID 178505475HCID 178505475, compound

Product 1

HCID 902164751-(5-tert-butyldimethylsiloxypentyl)-5-fluoro-3-iodo-1H-indazoleYield 79%

Procedure

The title compound was prepared from 5-fluoro-3-iodo-indazole and (5-chloropentoxy)tert-butyldimethylsilane in 79% yield according to the general procedure for Preparation 31A. The minor isomer was not isolated or characterized. 1H NMR (400 MHz, CDCl3): δ 0.06 (6H, s), 0.90 (9H, s), 1.34-1.37 (2H, m), 1.50-1.55 (2H, m), 1.90-1.94 (2H, m), 3.55 (2H, t, J=6.4 Hz), 4.37 (2H, t, J=7.2 Hz), 7.10 (1H, dd, J=2.0, 8.0 Hz), 7.19 (1H, td, J=2.4, 8.8 Hz), 7.432 (1H, dd, J=4.0, 9.2 Hz).

Workup

  1. customThe minor isomer was not isolated

Sources & evidence

ORD record
ord-737ab5ece2aa4093beecad95140c5263
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

Loading…