N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamide → HCID 117942080, compound

HRID 1499102Notes

Reaction equation

HRID 1499102 reaction equation
C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])=[C:30]([N:40]2[CH:44]=[CH:43][C:42]([CH3:45])=[N:41]2)[CH:29]=1.C([O-])=O.[K+]>O.C(#N)C.C[Ir-4](Cl)(C)(C)(C)(C)C1C=CC=C1>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]([OH:39])[C:35]([F:38])([F:37])[F:36])=[C:30]([N:40]2[CH:44]=[CH:43][C:42]([CH3:45])=[N:41]2)[CH:29]=1

Participants

7

Reactant 3

HCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideHCID 2735122Potassium FormateHCID 1179421121-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone

Product 1

HCID 117942080HCID 117942080, compound

Reagents, catalysts & solvents 3

HCID 178477776HCID 178477776, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Pentamethylcyclopentadienyl iridium (III) chloride dimer (CAS#12354-84-6) (10.4 mg) and (1R,2R)-(−)-N-(4-toluene sulfonyl)-1,2-diphenyl ethylene diamine (CAS#144222-34-4) (9.2 mg) were combined in water (120 mL), then heated to 50° C. for 5 h to provide the “Iridium complex.” 1-[4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethanone (16 g, 48 mmol) was dissolved in acetonitrile (120 mL) to which the Iridium complex and potassium formate (3.1 g, 3.7 mmol) were added. The reaction mixture was heated to 50° C. for 8 h. The reaction mixture was then cooled to RT, partitioned between water and EtOAc, and extracted. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Recrystallization from hot heptane (200 mL) provided the title compound.

Workup

  1. customto provide the “Iridium complex
  2. additionwere added
  3. temperatureThe reaction mixture was heated to 50° C. for 8 h
  4. temperatureThe reaction mixture was then cooled to RT
  5. custompartitioned between water and EtOAc
  6. extractionextracted
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customRecrystallization from hot heptane (200 mL)

Sources & evidence

ORD record
ord-89e44f85a3e4496ca1b80e58d5cb93fa
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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