Sodium hydride → HCID 86725264, compound

HRID 1478860Notes

Reaction equation

HRID 1478860 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-6157fe2a946b436684d289886d2d26f4
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

Loading…