Potassium Carbonate → HCID 59300741、化合物

反応式

[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].Br[CH2:21][C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+]>>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:21][C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

参加物

反応物 3

HCID 11430Potassium Carbonate

HCID 124940911-Bromo-4,4-dimethylpent-2-yne

HCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

生成物 1

HCID 59300741HCID 59300741、化合物収率 23.1%

実験手順

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (10.5 g) is alkylated using 1-bromo-4,4-dimethyl-pent-2-yne (7 g; 40 mmol) and K2CO3 (5.52 g; 40 mmol) at 40° C. for 16 h. After aqueous work-up and purification by RP chromatography the pure material (3.9 g) is de-acetylated in MeOH (250 ml) using DBU (3.58 g) at reflux. After aqueous work-up 5-amino-1-(4,4-dimethyl-pent-2-ynyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (2.9 g) is obtained and used without further purification.