Potassium Carbonate → HCID 59301022, compound

HRID 2235364Notes

Reaction equation

HRID 2235364 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].I[CH2:21][CH2:22][C:23]#[C:24][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]([CH2:25][CH2:24][C:23]#[C:22][CH3:21])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 10375356HCID 10375356, compoundHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59301022HCID 59301022, compoundYield 10.7%

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (3 g) is alkylated using 1-iodo-3-pentyne (4.42 g; 22.8 mmol) and K2CO3 (4.29 g; 30.4 mmol) at 40° C. for 5 d. After aqueous work-up and purification by RP chromatography a part of the material (0.4 g) is de-acetylated in MeOH (30 ml) using DBU (0.4 ml) at reflux. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-pent-3-ynyl-1,3-dihydro-indol-2-one (0.35 g) is obtained and used without further purification.

Workup

  1. customat 40° C.
  2. customfor 5 d
  3. customAfter aqueous work-up and purification by RP chromatography a part of the material (0.4 g)
  4. temperatureat reflux

Sources & evidence

ORD record
ord-f128baa0e7e44d8d9e6952f3ea594401
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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