N,N,N',N'-Tetramethylethylenediamine → HCID 70980241, compound

HRID 1475468Notes

Reaction equation

HRID 1475468 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.CN([CH2:15][CH2:16]N(C)C)C.[Li][CH2:21][CH2:22]CC>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:15][CH3:16])([CH2:21][CH3:22])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 178418339Butyllithium

Product 1

HCID 70980241HCID 70980241, compoundYield 23.2%

Procedure

Following similar methods to those described in Preparation 321 starting from 6-chloro-1,3-dihydro-indol-2-one (4 g, 25 mmol), TMEDA(11.2 mL, 79 mmol), BuLi (1.6M in hexane, 30 mL, 48 mmol) and Etl (2.9 mL, 36 mmol) gave the title compound (1.3 g). MS: [M+H]+=224.

Sources & evidence

ORD record
ord-2741f44eeae245a2830d1db4fb0c8606
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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