Triethylamine → (S)-N-(5-(3-(trifluoromethyl)phenoxy)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 473081Notes

Reaction equation

HRID 473081 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[OH:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][C@H:26]([NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH2:25]2>C(Cl)Cl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][C@H:26]([NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH2:25]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 70223439(S)-N-(5-(3-(trifluoromethyl)phenoxy)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of the 3-trifluoromethyphenyl boronic acid (0.274 mmol, 52 mg), copper (II) acetate (0.137 mmol, 25 mg), triethylamine (0.685 mmol, 96 μL) and 4A molecular sieves (100 mg) in DCM (1 mL) was added (S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.137 mmol, 35 mg) and the resultant mixture stirred at room temperature overnight. The reaction mixture was diluted with DCM (1 mL) before water (0.5 mL) was added and the organic layers separated using hydrophobic frits. The aqueous was extracted with a further 1 mL DCM, and the combined organics concentrated using to dryness. The residue was taken up in DMSO and purified by preparative HPLC to give the title compound as a clear film (21.9 mg, 40%). MS (ESI): m/z [M+H]+ 400.0

Workup

  1. additionwas added
  2. customthe organic layers separated
  3. extractionThe aqueous was extracted with a further 1 mL DCM
  4. concentrationthe combined organics concentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-78bf524ca8b8459bb604a3c0c12ce1a1
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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