Allyl bromide → HCID 23500765, compound

HRID 1835859Notes

Reaction equation

HRID 1835859 reaction equation
[CH2:1]([C:4]1(C(CC=C)NC)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13])[CH:2]=[CH2:3].N1C2C(=CC=CC=2)CC1=O.[O-]CC.[Na+].[H-].[Na+].C(Br)C=C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13])[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 321710OxindoleHCID 2723922Sodium ethoxideHCID 23500694HCID 23500694, compound

Product 1

HCID 23500765HCID 23500765, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Allyl-3-[allyl(methyl)aminomethyl]-indolin-2-one. Oxindole was acylated with ethyl acetate in the presence of sodium ethoxide as described (Chem. Abstr. 1953, 47, p7488). The crude product (9.16 g; 52.3 mmol) was treated with sodium hydride (56 mmol) in DMF at ice bath temperature for 30 min. Allyl bromide (51 mmol) was added and the reaction mixture left at room temperature overnight. The crude product after workup was purified by SGC (EtOAc/isohexanes 1:2). The acetyl group was removed by treatment with triethylamine/water 1:1 at 65° C. for 12 h and the the 3-allyloxindole thus obtained was treated with an excess of allylmethylamine and one equivalent of paraformaldehyde in acetic acid at 70 for 4 h. The crude material after evaporation of solvents was partioned between DCM and basic water. SGC using EtOAc/isohexanes 1:1 gave a reddish oil of the title product(83%).

Workup

  1. customThe crude product after workup was purified by SGC (EtOAc/isohexanes 1:2)
  2. customThe acetyl group was removed by treatment with triethylamine/water 1:1 at 65° C. for 12 h

Sources & evidence

ORD record
ord-46688c1a45944d1cb4c515f5da956cb2
Source dataset
uspto-grants-2004_08
Patent number
US06774132B1

Reaction notes

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