HCID 11192533, compound → N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)ethyl]-1-(3,4-dichlorophenyl)methanesulfonamide

HRID 2181491Notes

Reaction equation

HRID 2181491 reaction equation
[CH:1]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[C:22]#[C:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)(=[O:29])=[O:28])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cu]I.O>[CH:1]([N:14]1[C:15]2[C:16](=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:22]=[C:23]1[CH2:24][CH2:25][NH:26][S:27]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)(=[O:29])=[O:28])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 11192533HCID 11192533, compound

Product 1

HCID 11204051N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)ethyl]-1-(3,4-dichlorophenyl)methanesulfonamideYield 76.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-{4-[2-(benzhydrylamino)-5-chlorophenyl]but-3-ynyl}-1-(3,4-dichlorophenyl)-methanesulfonamide (1.0 g, 1.71 mmol) and copper (I) iodide (0.30 g, 1.58 mmol) was heated to 120° C. and stirred for 7 h, and then cooled to room temperature. Water (50 mL) was added. The mixture was extracted with EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4. The solvent was evaporated. The residue was purified by column chromatography, using a mixture of heptane and EtOAc (2:1) as elute to give a white solid (0.76 g, 76%). 1H NMR (CDCl3): δ6.7-7.6 (m, Ph. CHPh2), 6.58 (d, 1H, J=8.9 Hz), 4.20 (m, 1H), 3.99 (s, 2H), 3.10 (dd, 2H, J=6.9, 13.3 Hz), 2.94 (t, 2H, J=6.7 Hz).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. customThe solvent was evaporated
  5. customThe residue was purified by column chromatography
  6. additiona mixture of heptane and EtOAc (2:1)
  7. washas elute

Sources & evidence

ORD record
ord-5cca35351daa4815bb74e2a0021bfb20
Source dataset
uspto-grants-2005_05
Patent number
US06891065B2

Reaction notes

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