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

HRID 1964474Notes

Reaction equation

HRID 1964474 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, 1 H), 8.31 (d, J=7.5 Hz, 1 H), 7.02 (d, J=11.7 Hz, 1 H), 6.32 (s, 1 H), 3.63 (s, 2 H), 1.35 (s, 6 H), 0.99 (s, 9 H), 0.11 (s, 6 H).

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-186700f94bc94857b4cd6263458e633c
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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