Imidazole → 2-(1-((tert-Butyldimethylsilyl)oxy)-2-methylpropan-2-yl)-6-fluoro-5-nitro-1H-indole

HRID 1847924Notes

Reaction equation

HRID 1847924 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[NH:8]2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21].N1C=CN=C1>C(Cl)Cl>[Si:23]([O:13][CH2:12][C:11]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([N+:16]([O-:18])=[O:17])=[C:2]([F:1])[CH:10]=2)([CH3:15])[CH3:14])([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 591293832-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropan-1-ol

Product 1

HCID 591292962-(1-((tert-Butyldimethylsilyl)oxy)-2-methylpropan-2-yl)-6-fluoro-5-nitro-1H-indoleYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropan-1-ol (10.0 g) in CH2Cl2 was added TBSCl (8.9 g), imidazole (8.1 g, 0.12 mol) at room temperature. The mixture was stirred overnight. The solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel (10% EtOAc in petroleum ether) to give 2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-fluoro-5-nitro-1H-indole (5.3 g, 38%). 1H NMR (300 MHz, CDCl3) 9.51 (s, 1H), 8.31 (d, J=7.5 Hz, 1H), 7.02 (d, J=11.7 Hz, 1H), 6.32 (s, 1H), 3.63 (s, 2H), 1.35 (s, 6H), 0.99 (s, 9H), 0.11 (s, 6H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by chromatography on silica gel (10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c7e85a19568848a9b1e0c392ea83df80
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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