Sodium hydride → HCID 21833029, compound

HRID 1740748Notes

Reaction equation

HRID 1740748 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:18]/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C.O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH2:18]/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 21833029HCID 21833029, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-Acetyl-6-bromo-5-hydroxyindoline (Tetrahedron, 1973, 29 (8), 1115) (2.54 g, 10 mmol) was stirred under Ar in dry DMF (50 ml) as sodium hydride (80%, 0.33 g, 11 mmol) was added over 10 min. After a further 10 min, methyl 4-bromocrotonate (1.75 ml, 15 mmol) was added. The mixture was stirred at 60° C. for 2 h, cooled, and diluted with water. The precipitated material was filtered off and washed with water and ether, affording the title compound (2.40 g, 68%) as a brown solid. NMR showed a mixture of isomers (ca. 1:1).

Workup

  1. additionwas added over 10 min
  2. temperaturecooled
  3. filtrationThe precipitated material was filtered off
  4. washwashed with water and ether

Sources & evidence

ORD record
ord-215d83b5675643b88b411a9313bc44e4
Source dataset
uspto-grants-1999_10
Patent number
US05972935

Reaction notes

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