Dimethylformamide → (2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindolin-5-yl)prop-2-enamide

HRID 730266Notes

Reaction equation

HRID 730266 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[N+]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)N[CH2:21][CH2:20]2)([O-])=O.IC.[OH-].[Na+].CN([CH:33]=[O:34])C>O>[C:5]([C:25]1[CH:24]=[CH:23][C:19](/[CH:20]=[CH:21]/[C:33]([NH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[CH2:3][CH2:4]3)=[O:34])=[CH:18][CH:17]=1)([CH3:10])([CH3:6])[CH3:4]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 362195-NitroindolineHCID 1677381H-Indole, 2,3-dihydro-1-methyl-5-nitro-

Product 1

HCID 10236808(2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindolin-5-yl)prop-2-enamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Methyl-5-nitroindoline. To a round-bottomed flask equipped with magnetic stirring was added 5-nitroindoline (0.82, 5.0 mmol, Aldrich), iodomethane (0.71 g, 5.0 mmol, Aldrich), sodium hydroxide (0.24, 6 mmol) and DMF (20 mL). The reaction mixture was stirred at 25° C. for 3 h, diluted with water (50 mL), extracted with EtOAc (3×40 mL) and the combined extracts were concentrated in vacuo. Purification by silica gel chromatography 97:3 hexane:EtOAc) provided the title product. MS (ESI, pos. ion) m/z: 179 (M+1).

Workup

  1. customTo a round-bottomed flask equipped
  2. stirringThe reaction mixture was stirred at 25° C. for 3 h
  3. extractionextracted with EtOAc (3×40 mL)
  4. concentrationthe combined extracts were concentrated in vacuo
  5. customPurification by silica gel chromatography 97:3 hexane

Sources & evidence

ORD record
ord-d69981558afe4b55a756cf2deb7ad26b
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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