Water → HCID 67959813, compound

HRID 1529381Notes

Reaction equation

HRID 1529381 reaction equation
[H-].[Na+].[CH:3]1([C:6]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][CH:16]=[C:15]4[I:21])[CH:9]=[N:8][CH:7]=2)[CH2:5][CH2:4]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>C1COCC1>[CH:3]1([C:6]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[N:17]([S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[CH:16]=[C:15]4[I:21])[CH:9]=[N:8][CH:7]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 67959733HCID 67959733, compound

Product 1

HCID 67959813HCID 67959813, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% in mineral oil) (34 mg, 0.85 mmol) was added to a solution of 5-(6-cyclopropylpyrazin-2-yl)-3-iodo-1H-indole (280 mg, 0.78 mmol) in THF (4 mL) at 0° C. The mixture was stirred for 10 min at 0° C. and p-toluenesulfonyl chloride (163 mg, 0.85 mmol) was added and the mixture was warmed to RT. After 1 h, water was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to afford 5-(6-cyclopropylpyrazin-2-yl)-3-iodo-1-tosyl-1H-indole (394 mg, 0.76 mmol, 99% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 516.0 (M+1).

Workup

  1. temperaturethe mixture was warmed to RT
  2. waitAfter 1 h
  3. extractionthe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61cee6607abe46e3a176bb9da11eeda3
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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