3,3-Dimethylbutanoyl chloride → HCID 59754780, compound

HRID 1713430Notes

Reaction equation

HRID 1713430 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH3:25])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].[CH3:29][C:30]([CH3:36])([CH3:35])[CH2:31][C:32](Cl)=[O:33].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH3:25])=[CH:12][CH:13]=2)[C:8]=1[C:32](=[O:33])[CH2:31][C:30]([CH3:36])([CH3:35])[CH3:29])[CH3:2]

Participants

5

Reactant 3

HCID 815143,3-Dimethylbutanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59754773HCID 59754773, compound

Product 1

HCID 59754780HCID 59754780, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

3-[5-Methoxy-1-(4-chloro-benzyl)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (Example 5, Step 4; 0.133 g, 0.33 mmol) was dissolved in dichloroethane (5 mL). 3,3-Dimethyl-butyryl chloride (0.12 mL, 0.86 mmol) and aluminum chloride (0.137 g, 1.03 mmol) were added, and the reaction was heated to 80° C. under N2 for 1.5 hours. The reaction mixture was cooled to room temperature and quenched with saturated potassium sodium tartrate tetrahydrate solution. The mixture was extracted with EtOAc three times, the combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude material was purified on silica gel (0-50% EtOAc in hexanes) to give the desired product.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with saturated potassium sodium tartrate tetrahydrate solution
  3. extractionThe mixture was extracted with EtOAc three times
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d164f757968c4267a4312e80f145b0a2
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

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