Dimethylamine → HCID 59441803, compound

HRID 1014339Notes

Reaction equation

HRID 1014339 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][NH:9]2)=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23](Cl)=[O:24].[CH3:26][NH:27][CH3:28]>C1COCC1.C(OCC)(=O)C>[CH3:26][N:27]([CH3:28])[CH2:22][C:23]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:12]([O-:14])=[O:13])=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1)=[O:24]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 20430314HCID 20430314, compound

Product 1

HCID 59441803HCID 59441803, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(methyloxy)-5-nitro-2,3-dihydro-1H-indole (1.1 g, 5.67 mmol) and potassium carbonate (2.34 g, 17.17 mmol) in THF (250 mL) was added bromoacetyl chloride (0.98 g, 6.23 mmols) via a dropwise addition. After stirring 2 hrs at rt, catalytic Kl was added followed by a 2.0M solution of dimethylamine in tetrahydrofuran (17 mL). After overnight stirring, the reaction was diluted with ethyl acetate and washed with water (200 mL). The organic layer was adsorbed onto silica gel and purified by column chromatography (DCM to 10% MeOH/DCM) to afford N,N-dimethyl-2-[6-(methyloxy)-5-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine (0.55 g, 35% over two steps). ESIMS (M+H)+=280.

Workup

  1. additionvia a dropwise addition
  2. additioncatalytic Kl was added
  3. stirringAfter overnight stirring
  4. washwashed with water (200 mL)
  5. custompurified by column chromatography (DCM to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-c4dcbdf968624f568329802a220700a8
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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