tetrahydro-2H-pyran-3-ol → 5-fluoro-3-iodo-1-(tetrahydro-2H-pyran-3-yl)-1H-indazole

HRID 868880Notes

Reaction equation

HRID 868880 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].[O:12]1[CH2:17][CH2:16][CH2:15][CH:14](O)[CH2:13]1>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:14]1[CH2:15][CH2:16][CH2:17][O:12][CH2:13]1)[N:6]=[C:5]2[I:11]

Participants

3

Reactant 2

HCID 12256033tetrahydro-2H-pyran-3-olHCID 178505475HCID 178505475, compound

Product 1

HCID 867231685-fluoro-3-iodo-1-(tetrahydro-2H-pyran-3-yl)-1H-indazoleYield 23%

Procedure

The title compound was prepared from 5-fluoro-3-iodo-indazole and tetrahydro-3-pyranol in 23% yield according to the general procedure for Preparation 31A. The minor isomer was not isolated or characterized. 1H NMR (400 MHz, CDCl3): δ 1.86-1.93 (2H, m), 2.20-2.23 (1H, m), 2.34-2.41 (1H, m), 3.48-3.55 (1H, m), 3.80 (1H, t, J=10.4 Hz), 4.00-4.07 (2H, m), 4.50-4.58 (1H, m), 7.12 (1H, dd, J=2.4, 8.0 Hz), 7.21 (1H, td, J=2.4, 8.8 Hz), 7.39 (1H, dd, J=4.0, 8.8 Hz).

Workup

  1. customThe minor isomer was not isolated

Sources & evidence

ORD record
ord-f3f2e5705df245f285f4e5981aec82a3
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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