Imidazole → 5-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indole

HRID 1481698Notes

Reaction equation

HRID 1481698 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][OH:13])=[CH:5]2.N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][O:13][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:5]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57481472(5-bromo-1-methyl-1H-indol-2-yl)methanol

Product 1

HCID 712845855-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indoleYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-1-methyl-1H-indol-2-yl)methanol (7.8 g, ca. 31.3 mmol) in CH2Cl2 (80 mL) was added imidazole (2.6 g, 38.2 mmol, 1.2 eq) followed by TBS-Cl (5.2 g, 34.5 mmol, 1.1 eq) at 0° C. The reaction was monitored by LC-MS. After 1 h, the reaction was quenched with water then extracted by CH2Cl2 (3×50 mL). The solvent was concentrated to give a crude product which was purified by flash column chromatography (50% CH2Cl2 in hexanes) to afford the title compound (10.7 g, 30.2 mmol, 96%) over three steps as an off-white solid.

Workup

  1. customthe reaction was quenched with water
  2. extractionthen extracted by CH2Cl2 (3×50 mL)
  3. concentrationThe solvent was concentrated
  4. customto give a crude product which
  5. customwas purified by flash column chromatography (50% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-ba1dff77915447c58a1a4a8588bb7954
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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