Propargyl bromide → HCID 59300981, compound

HRID 2235376Notes

Reaction equation

HRID 2235376 reaction equation
[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]#[CH:23].C([O-])([O-])=O.[K+].[K+].C1CCN2C(=NCCC2)CC1>CO>[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]([CH2:23][C:22]#[CH:21])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300981HCID 59300981, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide is alkylated using 3-bromo-propyne and K2CO3. After aqueous work-up the crude material (5.11 g) is de-acetylated in MeOH (180 ml) using DBU (1,3 ml) at reflux. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-prop-2-ynyl-1,3-dihydro-indol-2-one (4.32 g) is obtained and used without further purification.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-6ab6d4af88454fcda78224d79d9102d8
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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