Potassium Carbonate → HCID 59300884, compound

HRID 2235375Notes

Reaction equation

HRID 2235375 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][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1.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]([CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 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 59300884HCID 59300884, 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 (2 g) is alkylated using 2-bromomethyl-tetrahydro-furan (1.7 ml; 15.2 mmol) and K2CO3 (2.1 g; 15.2 mmol) at 30° C. for 3 days. After aqueous work-up the crude material is de-acetylated in MeOH (150 ml) using DBU (2,3 ml) at reflux. After aqueous work-up and purification by RP chromatography 5-amino-3,3-dimethyl-6-nitro-1-(tetrahydro-furan-2-ylmethyl)-1,3-dihydro-indol-2-one (1.88 g) is obtained.

Workup

  1. customat 30° C.
  2. customfor 3 days
  3. temperatureat reflux
  4. customAfter aqueous work-up and purification by RP chromatography 5-amino-3,3-dimethyl-6-nitro-1-(tetrahydro-furan-2-ylmethyl)-1,3-dihydro-indol-2-one (1.88 g)
  5. customis obtained

Sources & evidence

ORD record
ord-cb28190d62b04e66bfdb72f57dc25441
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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