Ethyl Acetate → Methyl (3-(3-acetyl-1H-pyrazolo[3,4-b]pyridin-1-yl)propyl)carbamate

HRID 922465Notes

Reaction equation

HRID 922465 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10](=[O:12])[CH3:11])=[N:2]1.Br[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:21])[O:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[C:10]([C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:1]([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:21])[O:19][CH3:20])[N:2]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 254236Methyl(3-bromopropyl)carbamateHCID 178467502HCID 178467502, compound

Product 1

HCID 68310426Methyl (3-(3-acetyl-1H-pyrazolo[3,4-b]pyridin-1-yl)propyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(1H-pyrazolo[3,4-b]pyridin-3-yl)ethanone (500 mg) and methyl (3-bromopropyl)carbamate (912 mg) in N,N-dimethylformamide (5 mL) was added potassium carbonate (864 mg), and the mixture was stirred at room temperature for 3 days. To the reaction solution was added ethyl acetate, and the mixture was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=95/5→1/1) to give methyl [3-(3-acetyl-1H-pyrazolo-[3,4-b]pyridin-1-yl)propyl]carbamate) [REx(103-2)] (308 mg) as a red oil.

Workup

  1. washthe mixture was washed with saturated saline
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=95/5→1/1)

Sources & evidence

ORD record
ord-7ef44caf290f45588edbb8697ef74596
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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