Sodium Iodide → HCID 59426014, compound

HRID 252541Notes

Reaction equation

HRID 252541 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:27]#[N:28])=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=3)[N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[Na+].[I-].C(N(C(C)C)CC)(C)C>CC#N.O>[C:27]([C:9]1[C:8]2[C:12](=[CH:13][C:5]([O:4][CH2:3][CH2:2][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:6][CH:7]=2)[N:11]([CH2:14][CH3:15])[C:10]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=1)#[N:28]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 59425008HCID 59425008, compound

Product 1

HCID 59426014HCID 59426014, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of N-{4-[6-(2-chloroethoxy)-3-cyano-1-ethyl-1H-indol-2-yl]-phenyl}methanesulfonamide (90 mg, 0.21 mmol), morpholine (0.06 mL, 0.65 mmol), NaI (32 mg, 0.21 mmol) and diisopropyl ethylamine (0.06 mL, 0.32 mmol) in CH3CN (2 mL) is heated in a sealed tube at 100° C. for 25 h. The reaction mixture is cooled to room temperature, diluted with H2O and extracted with EtOAc (3×). The combined organic phases are washed with saturated NaCl, dried and concentrated. The crude solid is triturated with EtOAc and filtered to give 41 mg (41%) of N-{4-[3-cyano-1-ethyl-6-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-phenyl}methanesulfonamide as a tan solid.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic phases are washed with saturated NaCl
  3. customdried
  4. concentrationconcentrated
  5. customThe crude solid is triturated with EtOAc
  6. filtrationfiltered

Sources & evidence

ORD record
ord-096f36887c1e419788265ac48a13f78d
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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