Potassium Carbonate → HCID 59300725, compound

HRID 2235383Notes

Reaction equation

HRID 2235383 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].[C:20]([O:24][C:25]([NH:27][C:28]1[CH:39]=[CH:38][CH:37]=[CH:36][C:29]=1[CH2:30]OS(C)(=O)=O)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+].C1CCN2C(=NCCC2)CC1>CO>[C:20]([O:24][C:25](=[O:26])[NH:27][C:28]1[CH:39]=[CH:38][CH:37]=[CH:36][C:29]=1[CH2:30][N:4]1[C:5]2[C:10](=[CH:9][C:8]([NH2:11])=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=2)[C:2]([CH3:1])([CH3:19])[C:3]1=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 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)acetamideHCID 86601806HCID 86601806, compound

Product 1

HCID 59300725HCID 59300725, compoundYield 115.6%

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 (0.55 g) is alkylated using methanesulfonic acid 2-tert-butoxycarbonylamino-benzyl ester (0.69 g; 2.09 mmol) and K2CO3 (0.99 g; 7.19 mmol) at RT for 18 h. After aqueous work-up the crude material is de-acetylated in MeOH (50 ml) using DBU (0.3 ml) at reflux. After aqueous work-up [2-(5-amino-3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-indol-1-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (1.03 g) is obtained and used without further purification.

Workup

  1. customat RT
  2. customfor 18 h
  3. temperatureat reflux

Sources & evidence

ORD record
ord-daa13a90f1644877b316074744f528ee
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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