Sodium hydride → 6-(5-Cyano-2-hydroxy-1H-indol-3-yl)-N-methoxy-N-methylnicotinamide

HRID 1881330Notes

Reaction equation

HRID 1881330 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3]1.[H-].[Na+].Cl[C:16]1[CH:27]=[CH:26][C:19]([C:20]([N:22]([O:24][CH3:25])[CH3:23])=[O:21])=[CH:18][N:17]=1>CN(C=O)C>[C:11]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2]([OH:1])=[C:10]2[C:16]1[CH:27]=[CH:26][C:19]([C:20]([N:22]([O:24][CH3:25])[CH3:23])=[O:21])=[CH:18][N:17]=1)#[N:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 114355976-Chloro-N-methoxy-N-methylnicotinamide

Product 1

HCID 1362398576-(5-Cyano-2-hydroxy-1H-indol-3-yl)-N-methoxy-N-methylnicotinamideYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 473 mg (2.99 mmol) of 2-oxoindoline-5-carbonitrile in DMF (10 mL) were added 229 mg (5.73 mmol) of sodium hydride (60% on mineral oil) as a solid. After stirring the resulting suspension for 60 min at RT, a solution of 500 mg (2.49 mmol) of 6-chloro-N-methoxy-N-methylnicotinamide from example 1.1 in DMF (10 mL) was added slowly and the mixture was stirred for 80 min at 120° C. The reaction was cooled down to RT and a saturated solution of NH4CL (40 mL) was added and the resulting precipitate was collected by filtration. The precipitate was washed with water and hexane and afterwards dried in a vacuum oven. Yellow solid. Amount 265 mg. Yield 33%.

Workup

  1. stirringthe mixture was stirred for 80 min at 120° C
  2. temperatureThe reaction was cooled down to RT
  3. additiona saturated solution of NH4CL (40 mL) was added
  4. filtrationthe resulting precipitate was collected by filtration
  5. washThe precipitate was washed with water and hexane
  6. customafterwards dried in a vacuum oven

Sources & evidence

ORD record
ord-aa1660859cf0460d83d1a426d044d6fa
Source dataset
uspto-grants-2012_11
Patent number
US08318793B2

Reaction notes

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