HCID 52913256, compound → HCID 52913259, compound

HRID 540781Notes

Reaction equation

HRID 540781 reaction equation
[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[C:6](I)[C:5]([C:20]2[CH:21]=[C:22]([C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[N:4]1)[CH3:2]>[C-]#CC1C=CC=CC=1.[Cu+].N1C=CC=CC=1>[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[C:6]([C:6]#[C:5][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:5]([C:20]2[CH:21]=[C:22]([C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[N:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 52913256HCID 52913256, compound

Product 1

HCID 52913259HCID 52913259, compound

Reagents, catalysts & solvents 2

HCID 447869613146-23-1CatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-[2-(3-{1-ethyl-4-iodo-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)propan-2-yl]-2,2,2-trifluoroethanesulfonamide (51.2 mg, 0.077 mmol) and pyridine (387 μL) was treated with copper (I) phenylacetylide (12 mg, 0.085 mmol), degassed with argon, sealed in a microwave vial and heated to 100° C. via a block heater. After 2 days the resulting brown solution was cooled, diluted with EtOAc, washed with 50% sat. aq. NaHCO3 2×, sat. aq NaHCO3, dried (MgSO4) and concentrated to afford a black residue purified via MPLC, 10 g silica, 5-30% EtOAc in heptanes to afford a light yellow solid: MS: cal'd 636 (MH+), exp 636 (MH+).

Workup

  1. customdegassed with argon
  2. customsealed in a microwave vial
  3. temperatureAfter 2 days the resulting brown solution was cooled
  4. additiondiluted with EtOAc
  5. washwashed with 50% sat. aq. NaHCO3 2×, sat. aq NaHCO3
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto afford a black residue
  9. custompurified via MPLC, 10 g silica, 5-30% EtOAc in heptanes
  10. customto afford a light yellow solid

Sources & evidence

ORD record
ord-c65b7857e17345a9b602b72dfb399bbc
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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