Potassium Carbonate → HCID 59425535, compound

HRID 907173Notes

Reaction equation

HRID 907173 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]2[N:13]([CH2:25][CH3:26])[C:14]3[C:19]([C:20]=2[C:21]#[N:22])=[CH:18][CH:17]=[C:16]([O:23][CH3:24])[CH:15]=3)[CH:9]=[CH:8][C:7]=1[OH:27])=[O:4].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:25]([N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([O:23][CH3:24])[CH:15]=2)[C:20]([C:21]#[N:22])=[C:12]1[C:10]1[CH:9]=[CH:8][C:7]2[O:27][CH2:2][C:3](=[O:4])[NH:5][C:6]=2[CH:11]=1)[CH3:26]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59430591HCID 59430591, compound

Product 1

HCID 59425535HCID 59425535, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloro-N-[5-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-2-hydroxy-phenyl] acetamide (57 mg, 0.13 mmol), prepared in step A, was combined with K2CO3 (55 mg, 0.4 mmol), and DMF (400 μL). This was heated at 80° C. for 1 hour. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica gel chromatography (9/1, CH2Cl2/EtOAc) yielded 1-ethyl-6-methoxy-2-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-indole-3-carbonitrile (45 mg, 90%) as a white solid.

Workup

  1. customThe reaction mixture was then partitioned between H2O and EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (9/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-d737db8fc8af4d56986aeb3730c47cb4
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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