Ethanol → HCID 86720580, compound

HRID 513208Notes

Reaction equation

HRID 513208 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)=[C:9]([C:25]([O:27]CC)=[O:26])[N:8]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:7]=12.CCO.O.[Li+].[OH-]>C1COCC1>[C:33]([O:32][C:30]([N:8]1[C:7]2=[C:2]([Cl:1])[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:16][CH:15]=2)=[C:9]1[C:25]([OH:27])=[O:26])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 86720579HCID 86720579, compound

Product 1

HCID 86720580HCID 86720580, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butyl 2-ethyl 7-chloro-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-1,2-dicarboxylate (33 mg, 0.06 mmol) in THF (1 mL) was added EtOH (0.2 mL)m and water (0.2 mL). Solid LiOH (30 mg, 1.2 mmol) was then added in a single portion. After 2.5 h, quenched with 5% potassium bisulfate until acidic (˜pH 3) and extracted with Et2O and then EtOAc. The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo to yield the title compound (30 mg). LRMS (ESI) calc (M+H)+=501.1. found 501.2.

Workup

  1. customquenched with 5% potassium bisulfate until acidic (˜pH 3)
  2. extractionextracted with Et2O
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4ca9faaad874ab68cd81c392c15856b
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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