Sodium Formate → HCID 85789495, compound

HRID 392436Notes

Reaction equation

HRID 392436 reaction equation
I[C:2]1[CH:3]=[C:4]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:22]([O-])=[O:23].[Na+]>CN(C=O)C>[CH:22]([C:2]1[CH:3]=[C:4]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8])=[O:23]

Participants

4

Reactant 2

HCID 2723810Sodium FormateHCID 23521705HCID 23521705, compound

Product 1

HCID 85789495HCID 85789495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(3-iodo-4-methylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.415 g, 0.997 mmol), sodium formate (0.102 g, 1.50 mmol), and dichloro-bis(triphenylphosphine)palladium (0.014 g, 0.020 mmol) were combined in 1.0 mL DMF and purged with anhydrous CO gas. The mixture was heated to 100° C. for 1.5 h. The reaction was poured into saturated NaHCO3 solution and extracted with EtOAc. The combined fractions were washed with H2O and brine, dried over MgSO4, filtered and concentrated. The mixture was chromatographed on silica gel with 1:1 EtOAc/DCM to give the title compound as a clear oil. 1H NMR: 10.11 (s,1H), 8.38 (br s,1H), 8.26 (br s,1H). 7.60 (m,2H), 7.13 (m,1H), 7.00 (s,2H), 4.80 (s,2H), 3.00 (q,J=7.3 Hz, 2H), 2.52 (s,3H), 2.35 (t,J=7.3 Hz, 3H).

Workup

  1. custompurged with anhydrous CO gas
  2. additionThe reaction was poured into saturated NaHCO3 solution
  3. extractionextracted with EtOAc
  4. washThe combined fractions were washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe mixture was chromatographed on silica gel with 1:1 EtOAc/DCM

Sources & evidence

ORD record
ord-101312606bb947c0af0ab6748aad6602
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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