Methyl iodide → 1-ethyl-6-methoxy-2-[4-(5-methyl-1,1-dioxo-1lambda6-[1,2,5]thiadiazolidin-2-yl)-phenyl]-1H-indole-3-carbonitrile

HRID 907197Notes

Reaction equation

HRID 907197 reaction equation
[O:1]=[S:2]1(=[O:28])[NH:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH2:26][CH3:27])[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH3:25])[CH:16]=3)=[CH:9][CH:8]=1.[C:29](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[CH2:26]([N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:24][CH3:25])[CH:16]=2)[C:21]([C:22]#[N:23])=[C:13]1[C:10]1[CH:9]=[CH:8][C:7]([N:3]2[CH2:4][CH2:5][N:6]([CH3:29])[S:2]2(=[O:1])=[O:28])=[CH:12][CH:11]=1)[CH3:27]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59426210HCID 59426210, compound

Product 1

HCID 594259571-ethyl-6-methoxy-2-[4-(5-methyl-1,1-dioxo-1lambda6-[1,2,5]thiadiazolidin-2-yl)-phenyl]-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-yl)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (34 mg, 0.086 mmol) in anhydrous DMF (1.0 mL) was added potassium carbonate (25 mg, 0.18 mmol) and iodomethane (20.4 mg, 0.144 mmol). The mixture was stirred at room temperature for 2 h. and then diluted with water (6.0 mL) to give a precipitate. The precipitate was filtered, washed with water and dried to give 1-ethyl-6-methoxy-2-[4-(5-methyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-yl)-phenyl]-1H-indole-3-carbonitrile, compound 726, as a white solid (35 mg, 98% yield).

Workup

  1. customto give a precipitate
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-fd4bd647d0694d3ca4c661561b6ccd8a
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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