Ethanol → HCID 11379978, compound

HRID 2054343Notes

Reaction equation

HRID 2054343 reaction equation
C1(=O)[N:5]([CH2:6][CH:7]([C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][N:18]=3)[O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)C(=O)C2=CC=CC=C12.CCO>>[NH2:5][CH2:6][CH:7]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][N:18]=2)[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1

Participants

3

Reactant 2

HCID 702EthanolHCID 59655782HCID 59655782, compound

Product 1

HCID 11379978HCID 11379978, compoundYield 100%

Procedure

To a solution of 2-[2-Phthalimido-1-(2,3,5,6-tetrahydropyran-2-yl)oxyethyl]-7-azaindole (10.2 g, 26 mmol) in EtOH (630 ml) NH2NH2.H2O (1.53 ml, 31 mmol) was added. The mixture was refluxed for 3 h. The solvent was evaporated, the residue dissolved in CH2Cl2 and washed with saturated aq. NaHCO3. The aqueous layer was extracted three times with CH2Cl2. The organic solutions were evaporated together to obtain a diastereomeric mixture (1:1) of 9a (6.72 g, 100%) as a light orange solid.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in CH2Cl2
  4. washwashed with saturated aq. NaHCO3
  5. extractionThe aqueous layer was extracted three times with CH2Cl2
  6. customThe organic solutions were evaporated together

Sources & evidence

ORD record
ord-a38ae243f7c442db9274fe8df09649a0
Source dataset
uspto-grants-2008_02
Patent number
US07329666B2

Reaction notes

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