Sodium Methoxide → 2-((6-chloro-4-(hydroxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)oxy)ethanol

HRID 588112Notes

Reaction equation

HRID 588112 reaction equation
C([O:4][CH2:5][C:6]1[C:11]2[C:12]([O:34][CH2:35][CH2:36][OH:37])=[N: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:38])[N:7]=1)(=O)C.C[O-].[Na+]>CO.C(Cl)Cl>[Cl:38][C:8]1[N:7]=[C:6]([CH2:5][OH:4])[C:11]2[C:12]([O:34][CH2:35][CH2:36][OH:37])=[N:13][N:14]([C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:10]=2[CH:9]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 118271833(6-chloro-3-(2-hydroxyethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate

Product 1

HCID 1182724112-((6-chloro-4-(hydroxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)oxy)ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (6-chloro-3-(2-hydroxyethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate (491.9 mg, 0.932 mmol) in MeOH (2 ml) and DCM (2 ml) was charged with sodium methoxide (25 wt % in MeOH, 0.45 ml, 1.968 mmol) and stirred at RT for 2 hr. Quenched with sat aq NH4Cl and extracted 3× with DCM. Washed organics with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 2-((6-chloro-4-(hydroxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)oxy)ethanol. MS: [M+H]+ m/z 486.

Workup

  1. customQuenched with sat aq NH4Cl
  2. extractionextracted 3× with DCM
  3. dry with materialWashed organics with brine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a65faacb639a4db8aaa233a83cc596f7
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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