N,N-Dimethylglycine → HCID 178504857, compound

HRID 588194Notes

Reaction equation

HRID 588194 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](I)=[N:9][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:4]=2[CH:3]=1.CN(C)CC(O)=O.[CH3:38][S:39]([O-:41])=[O:40].[Na+]>[Cu]I.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([S:39]([CH3:38])(=[O:41])=[O:40])=[N:9][NH:10][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 2733271Sodium methanesulfinateHCID 895258586-Chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine2×

Product 1

HCID 178504857HCID 178504857, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

6-Chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (Intermediate 13B; 1.0 g, 1.917 mmol), N,N-dimethylglycine (39.5 mg, 0.383 mmol), copper(I) iodide (36.5 mg, 0.192 mmol), and sodium methanesulfinate (276 mg, 2.300 mmol) were combined in a 20 mL microwave tube, evacuated under N2 and charged with DMSO (7.7 mL). The reaction was degassed via vacuum under nitrogen (×3) and irradiated in a microwave reactor to 110° C. for 90 min. The crude reaction mixture was poured into water and filtered. The precipitate was purified by flash chromatography (10-50% EtOAc/DCM) to afford 6-chloro-3-(methylsulfonyl)-1H-pyrazolo[4,3-c]pyridine. MS ESI calc'd. For C7H6ClN3O2S [M+1]+ 232. found 232.

Workup

  1. customevacuated under N2
  2. additioncharged with DMSO (7.7 mL)
  3. customThe reaction was degassed via vacuum under nitrogen (×3)
  4. customirradiated in a microwave reactor to 110° C. for 90 min
  5. customThe crude reaction mixture
  6. filtrationfiltered
  7. customThe precipitate was purified by flash chromatography (10-50% EtOAc/DCM)

Sources & evidence

ORD record
ord-d820402f674541d3a7fe9663737df1cb
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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