tert-Butyl(3-chloropropoxy)dimethylsilane → 1-(3-tert-butyldimethylsiloxypropyl)-5-fluoro-3-iodo-1H-indazole

HRID 868864Notes

Reaction equation

HRID 868864 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][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>>[O: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:17]([C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:18])[CH3:19]

Participants

3

Reactant 2

HCID 11009160tert-Butyl(3-chloropropoxy)dimethylsilaneHCID 178505475HCID 178505475, compound

Product 1

HCID 902170551-(3-tert-butyldimethylsiloxypropyl)-5-fluoro-3-iodo-1H-indazoleYield 79%

Procedure

The title compound was prepared from 5-fluoro-3-iodo-indazole and (3-chloropropoxy)tert-butyldimethylsilane (Org. Lett., 2000, 3473) 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), 0.89 (9H, s), 2.07-2.13 (2H, m), 3.55 (2H, t, J=6.0 Hz), 4.49 (2H, t, J=6.0 Hz), 7.10 (1H, dd, J=2.4, 8.4 Hz), 7.18 (1H, td, J=2.4, 8.8 Hz), 7.40 (1H, dd, J=4.0, 8.8 Hz).

Workup

  1. customThe minor isomer was not isolated

Sources & evidence

ORD record
ord-72da4cda1146472dadf96acd907acc99
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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