Imidazole → HCID 71285327, compound

HRID 1481736Notes

Reaction equation

HRID 1481736 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][OH:13])=[CH:5]2.N1C=CN=C1.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][O:13][Si:23]([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:25])[CH3:24])=[CH:5]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 70037385HCID 70037385, compound

Product 1

HCID 71285327HCID 71285327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of 2-(5-bromo-1H-indol-2-yl)ethanol (11.37 g, 47.36 mmol) in DCM (150 mL) was added imidazole (4.0 g, 58.75 mmol). Reaction mixture was cooled to 0° C. before solution of TBSCl (8.60 g, 57.06 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 30 min. The mixture was then diluted with DCM (150 mL), washed with H2O (100 mL) and NaCl (aqueous saturated, 100 mL) and the organic phase was dried over Na2SO4. The solvent was concentrated to afford 5-bromo-2-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indole which was used directly in the next step. LC-MS 354.2/356.2 [M+H]+, RT 1.85 min.

Workup

  1. customReaction mixture
  2. additionwas added dropwise
  3. washwashed with H2O (100 mL) and NaCl (aqueous saturated, 100 mL)
  4. dry with materialthe organic phase was dried over Na2SO4
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-ca58773dabe24acebfadf1a02c10de65
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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