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 506100Notes

Reaction equation

HRID 506100 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-f1e32c11ea144df3b19f3586956ce8e0
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

Loading…