Benzyl Bromide → 3-(benzyloxy)-6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588106Notes

Reaction equation

HRID 588106 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9](=[O:31])[NH:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C>[CH2:38]([O:31][C:9]1[C:5]2[C:6]([CH3:8])=[N:7][C:2]([Cl:1])=[CH:3][C:4]=2[N:11]([C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:10]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1182721366-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one2×

Product 1

HCID 1182720413-(benzyloxy)-6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one (16.10 g, 37.8 mmol, Intermediate 4B), potassium carbonate (17.75 g, 128 mmol) and benzyl bromide (6.3 ml, 53.0 mmol) in DMF (100 ml) was stirred at RT for 2 hr. Quenched with water and extracted into ether. Washed organics with brine, dried over MgSO4, filtered, concentrated in vacuo and triturated with hexanes to provide 3-(benzyloxy)-6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine. MS: [M+H]+ m/z 516.

Workup

  1. customQuenched with water
  2. extractionextracted into ether
  3. dry with materialWashed organics with brine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customtriturated with hexanes

Sources & evidence

ORD record
ord-19251e10ad924726b5fb5508358644f9
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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