Phosphorus oxychloride → HCID 178498049, compound

HRID 1522521Notes

Reaction equation

HRID 1522521 reaction equation
CC([N:5]1[C:9]2[N:10]=[C:11](O)[CH:12]=[C:13]([C:14]([O:16][CH2:17]C)=[O:15])[C:8]=2[C:7]([CH3:20])=[N:6]1)(C)C.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:11]1[CH:12]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:8]2[C:7]([CH3:20])=[N:6][NH:5][C:9]=2[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469343HCID 178469343, compound

Product 1

HCID 178498049HCID 178498049, compound

Procedure

Ethyl 1-(1,1-dimethylethyl)-3-methyl-6-hydroxy-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (2 g, 7.21 mmol) and phosphorus oxychloride (10 ml, 107 mmol) were heated at 100° C. for 32 hours. Ice was added and the contents were extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (eluent: 0% to 50% gradient EtOAc:Hex). The product was collected as 310 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (t, J=7.20 Hz, 3 H), 2.58 (s, 3 H), 4.44 (q, J=7.16 Hz, 2 H), 7.53 (s, 1 H), 13.82 (br. s., 1 H). LCMS(ES) [M+H]+240.1

Workup

  1. additionIce was added
  2. extractionthe contents were extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified via silica gel chromatography (eluent: 0% to 50% gradient EtOAc:Hex)
  8. customThe product was collected as 310 mg

Sources & evidence

ORD record
ord-dce2d08071dd46ec94308338009f9adf
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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