2-Bromoethanol → (6-chloro-3-(2-hydroxyethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate

HRID 588111Notes

Reaction equation

HRID 588111 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12](=[O:34])[NH:13][N:14]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[C:8]([Cl:35])[N:7]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][CH2:44][OH:45]>CN(C=O)C>[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12]([O:34][CH2:43][CH2:44][OH:45])=[N:13][N:14]([C:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[C:8]([Cl:35])[N:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 118272544(6-chloro-3-oxo-1-trityl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate

Product 1

HCID 118271833(6-chloro-3-(2-hydroxyethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (6-chloro-3-oxo-1-trityl-2,3-dihydro-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate (504.6 mg, 1.043 mmol) and potassium carbonate (558.3 mg, 4.04 mmol) in DMF (10 ml) was charged with 2-bromoethanol (0.30 ml, 4.25 mmol) and stirred at RT for 6 hr. Quenched with water and extracted 3× with Et2O. Washed organics with brine, dried over MgSO4, filtered and concentrated in vacuo. Purified via flash chromatography (0-100% EtOAc/Hex) to provide (6-chloro-3-(2-hydroxyethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate. MS: [M+H]+ m/z 528.

Workup

  1. customQuenched with water
  2. extractionextracted 3× with Et2O
  3. dry with materialWashed organics with brine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurified via flash chromatography (0-100% EtOAc/Hex)

Sources & evidence

ORD record
ord-e7fbd7cc689b4b73b2451f2b3b91f1e2
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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