Sodium hydride → Ethyl alpha-(5-fluoro-2-methyl-1-indolyl)propionate

HRID 980017Notes

Reaction equation

HRID 980017 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:13])=[CH:7]2.Br[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]([CH3:13])=[CH:7]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionateHCID 27787155-Fluoro-2-methylindole

Product 1

HCID 13755390Ethyl alpha-(5-fluoro-2-methyl-1-indolyl)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 322 g. (0.81 mole) of a 60% mineral oil dispersion of sodium hydride in 250 ml. of dry DMF was added dropwise a solution of 100 g. (0.67 mole) of 5-fluoro-2-methylindole in 300 ml. of dry DMF. The mixture was stirred at ambient temperature for thirty minutes and then treated dropwise with cooling with a solution of 121.5 g. (0.67 mole) of ethyl α-bromopropionate. Workup of the reaction mixture, after quenching with water and extraction of the product with ethyl acetate, afforded ethyl α-(5-fluoro-2-methyl-1-indolyl)-propionate.

Workup

  1. additionTo a stirred suspension of 322 g
  2. additiontreated dropwise
  3. temperaturewith cooling with a solution of 121.5 g
  4. customWorkup of the reaction mixture, after quenching with water and extraction of the product with ethyl acetate

Sources & evidence

ORD record
ord-5a0f127892f6424584fc4204d4b5f8e1
Source dataset
uspto-grants-1987_01
Patent number
US04634776

Reaction notes

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