Imidazole → HCID 21950027, compound

HRID 2215809Notes

Reaction equation

HRID 2215809 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2.N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[Si:19]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 55267831HCID 55267831, compound

Product 1

HCID 21950027HCID 21950027, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-hydroxypropyl-1H-indole (4.45 g, 25.4 mmol) in methylene chloride (50 mL), was added imidazole (2.31 g, 34.0 mmol), followed by tert-butyldimethylsilyl chloride (5.44 g, 36.1 mmol). The reaction mixture was stirred at room temperature for 12 h, filtered and concentrated to a brown oil. Flash chromatography (SiO2, 10% EtOAc/hexanes) gave the title compound (4.9 g, 66%) as a colorless oil. 1H NMR (300 MHz, CDCl3) 9.38 (bs, 1H), 7.54 (m, 1H), 7.22 (m, 1H), 7.18–6.06 (m, 2H), 6.60 (m, 1H), 3.71 (m, 2H), 3.07 (m, 2H), 1.98 (m, 2H), 1.03 (s, 9H), 0.20 (s, 6H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-37e62f63d6034063834757d78d5887db
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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