Formic Acid → HCID 117737071, compound

HRID 1504502Notes

Reaction equation

HRID 1504502 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19]([NH:22][C:23]3[CH:27]=[CH:26][O:25][N:24]=3)(=[O:21])=[O:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]1=[O:28].CN(C=O)C.C(O)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([NH:22][C:23]4[CH:27]=[CH:26][O:25][N:24]=4)(=[O:20])=[O:21])=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:28])=[CH:2][CH:7]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 6228DimethylformamideHCID 117737255HCID 117737255, compound

Product 1

HCID 117737071HCID 117737071, compoundYield 129.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A vial was charged with 1-(2-bromo-4-chlorophenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (202.5 mg, 0.320 mmol) and tetrakis(triphenylphosphine)palladium(0) (37.0 mg, 0.032 mmol). The vial was flushed with Ar (g), then DMF (1.6 mL) and formic acid (123 μl, 3.20 mmol) were added. The vial was sealed and placed in an 80° C. heating bath for 27 hrs. The mixture was cooled to rt and was loaded onto a 4-g silica gel loading column with the aid of MeOH/DCM, and the column was dried was dried under vauum. The column was then eluted onto a 25-g SNAP Ultra column with 0-50% of a 3:1 EtOAc/EtOH in heptane with 10% DCM to give 166 mg of 1-(4-chlorophenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide contaminated with some DMF and starting material. m/z (ESI) 402.2 (M+H)+.

Workup

  1. customThe vial was flushed with Ar (g)
  2. customThe vial was sealed
  3. customplaced in an 80° C.
  4. temperatureheating bath for 27 hrs
  5. customthe column was dried
  6. customwas dried under vauum
  7. washThe column was then eluted onto a 25-g SNAP Ultra column with 0-50% of a 3:1 EtOAc/EtOH in heptane with 10% DCM

Sources & evidence

ORD record
ord-feb8b7fb77fc4ce991602f4c58664a6d
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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