Potassium Carbonate → HCID 59300754, compound

HRID 2235384Notes

Reaction equation

HRID 2235384 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]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([F:30])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>Cl>[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]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([F:30])[CH:23]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27745534-(Bromomethyl)-2-fluoro-1-methoxybenzeneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300754HCID 59300754, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (0.57 g) is alkylated using 4-bromomethyl-2-fluoro-1-methoxy-benzene (0.5 g; 2.28 mmol) and K2CO3 (0.9 g; 6.52 mmol) at RT for 18 h. After aqueous work-up the crude material is de-acetylated in hydrochloric acid (20 ml; 6 N) at reflux. After aqueous work-up 5-amino-1-(3-fluoro-4-methoxy-benzyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (0.68 g) is obtained and used without further purification.

Workup

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

Sources & evidence

ORD record
ord-223c4d7adeba4ef29ffe56da23cedc2e
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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