tert-Butyldimethylsilyl chloride → HCID 90216531, compound

HRID 868871Notes

Reaction equation

HRID 868871 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[CH2:13][CH:14]([OH:16])[CH3:15].[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:16]([CH:14]([CH3:15])[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]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 297401-Bromo-2-propanolHCID 178505475HCID 178505475, compound

Product 1

HCID 90216531HCID 90216531, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in 31% yield from 5-fluoro-3-iodo-indazole and 1-bromo-2-propanol according to the general procedure for Preparation 11A, followed by alcohol protection using TBDMS chloride (1.1 eq) and DMAP (1.1 eq) in DCM. 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-0978e75a1ffc4798adf4fd9828d63b13
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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