Sodium hydride → HCID 86725264, compound

HRID 576631Notes

Reaction equation

HRID 576631 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[C:16]([NH:23][CH2:24][CH2:25]Br)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH2:25][CH2:24][NH:23][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 639844Methyl indole-6-carboxylateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 86725264HCID 86725264, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1H-Indole-6-carboxylic acid methyl ester (0.503 g, 2.87 mmol) and DMF (9.0 mL) under argon was cooled to 0° C. for 10 min. Sodium hydride (˜48%, 0.190 g, 3.80 mmol) was added and reaction warmed to room temperature for 30 min. 2-(Boc-amino)ethyl bromide (0.787 g, 3.52 mmol) was added and the reaction stirred for 17 hr. The reaction was quenched with H2O and extracted with ethyl acetate (3×). The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (0-50% EtOAc:Hexane). ESI-MS m/z 319 (MH)+.

Workup

  1. customreaction
  2. customThe reaction was quenched with H2O
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography on silica gel (0-50% EtOAc:Hexane)

Sources & evidence

ORD record
ord-6eb3923a914a4473ae3ad38e63aad15d
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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