Imidazole → HCID 59129412, compound

HRID 1847917Notes

Reaction equation

HRID 1847917 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][OH:14])[NH:8]2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>C(Cl)Cl>[Si:24]([O:14][CH2:13][CH2:12][C:11]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([N+:17]([O-:19])=[O:18])=[C:2]([F:1])[CH:10]=2)([CH3:16])[CH3:15])([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 591293673-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol

Product 1

HCID 59129412HCID 59129412, compoundYield 52,558,400%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol (6.6 g, 25 mmol) in CH2Cl2 (80 mL) was added TBSCl (3.7 g, 25 nmol) and imidazole (4.2 g, 62 nmol) at 0° C. The reaction mixture was stirred at room temperature for 12 hours. The precipitate was filtered off and washed with the methanol. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1) to give the desired product as a brown solid (5.0 g, 53%). 1H NMR (300 MHz, CDCl3) δ 9.80 (brs, 1H), 8.30 (d, J=7.2 Hz, 1H), 7.05 (d, J=11.7 Hz, 1H), 6.33 (t, J=1.2 Hz, 1H), 3.7 (t, J=6.0 Hz, 2H), 1.91 (t, J=6.0 Hz, 2H), 1.42 (s, 6H), 0.94 (s, 9H), 0.12 (s, 6H). MS (ESI) m/z (M+H+): 381.1.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with the methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-d2ced08a734b4614b34dae4786027a99
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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