Isopropyl iodide → HCID 66828962, compound

HRID 1046489Notes

Reaction equation

HRID 1046489 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[C:13]3[C:14]([O:18][CH3:19])=[N:15][CH:16]=[CH:17][C:12]=3[N:11]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:10]=2)[CH:6]=[C:5]1[C:39]([OH:41])=[O:40])([CH3:3])[CH3:2].I[CH:43]([CH3:45])[CH3:44].C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C>C1COCC1.O>[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[C:13]3[C:14]([O:18][CH3:19])=[N:15][CH:16]=[CH:17][C:12]=3[N:11]([C:20]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:10]=2)[CH:6]=[C:5]1[C:39]([O:41][CH:43]([CH3:45])[CH3:44])=[O:40])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 66825369HCID 66825369, compound

Product 1

HCID 66828962HCID 66828962, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-isopropyl-4-(4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)-1H-pyrrole-2-carboxylic acid (200 mg, 0.37 mmol), 2-iodopropane (310 mg, 1.80 mmol), Cs2CO3 (360 mg, 1.1 mmol) in THF (50 mL) was stirred at reflux for 6 hours. After cooling down, ethyl acetate (100 mL) and water (50 mL) were added. The organic layer was separated and washed by water (30 mL) and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound as a yellowish oil (100 mg).

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureAfter cooling down
  3. customThe organic layer was separated
  4. washwashed by water (30 mL) and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93c22995b367473b8c90b4ceb48a586a
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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