Ethyl Acetate → HCID 67203261, compound

HRID 1615388Notes

Reaction equation

HRID 1615388 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][NH:16]3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:19]([O:25][CH2:26][N:27]1[C:31]2[N:32]=[CH:33][N:34]=[C:35](Cl)[C:30]=2[CH:29]=[CH:28]1)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:19]([O:25][CH2:26][N:27]1[C:31]2[N:32]=[CH:33][N:34]=[C:35]([N:16]3[C:17]4[C:13](=[CH:12][CH:11]=[C:10]([C:6]5[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=5)[CH:18]=4)[CH:14]=[CH:15]3)[C:30]=2[CH:29]=[CH:28]1)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 57868847Propanoic acid, 2,2-dimethyl-, (4-chloro-7H-pyrrolo(2,3-d)pyrimidin-7-yl)methyl esterHCID 66955149HCID 66955149, compound

Product 1

HCID 67203261HCID 67203261, compoundYield 89.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6-(3-Nitrophenyl)-1H-indole (100 mg, 0.42 mmol) and (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (112 mg, 0.42 mmol) were dissolved in 1,4-dioxane (5 mL) in a sealed reactor and then Cs2CO3 (270 mg, 0.83 mmol) was added. After removing the gas included in the solution using ultrasonic wave and sequentially adding Xantphos (CAS No. 161265-03-8; 49 mg, 0.084 mmol) and Pd(OAc)2 (9.4 mg, 0.042 mmol), the reaction mixture was stirred at 120° C. for 2 hours. After cooling to room temperature and adding ethyl acetate and water, the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, methylene chloride 100%) yielded (4-(6-(3-nitrophenyl)-1H-indol-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (177 mg, 0.377 mmol) as white solid.

Workup

  1. customAfter removing the gas
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by column chromatography (silica gel, methylene chloride 100%)

Sources & evidence

ORD record
ord-c23692d379c844afb7efa2683dba4b67
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

Loading…