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 1009630Notes

Reaction equation

HRID 1009630 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) is added potassium carbonate (25 mg, 0.18 mmol) and iodomethane (20.4 mg, 0.144 mmol). The mixture is stirred at room temperature for 2 h and then diluted with water (6.0 mL) to give a precipitate. The precipitate is 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 is filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a98217d95eeb47e6a51b22a94bb6dae2
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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