HCID 46183926, compound → HCID 46183928, compound

HRID 341304Notes

Reaction equation

HRID 341304 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[C:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:17]=3)[C:12]3[CH:27]=[C:28]([Cl:31])[CH:29]=[N:30][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:17]=3)[C:12]3[CH:27]=[C:28]([Cl:31])[CH:29]=[N:30][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 46183926HCID 46183926, compound

Product 1

HCID 46183928HCID 46183928, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 9-benzenesulfonyl-3-chloro-6-(2-phenylethynyl)-9H-pyrido[2,3-b]indole (200 mg, 0.45 mmol, 1 equiv.) in anhydrous ethanol (25 ml) was treated with 10% palladium on carbon (50 mg, 0.047 mmol, 0.1 equiv.) and then stirred at room temperature under an atmosphere of H2 overnight. The reaction mixture was filtered through celite and then concentrated under reduced pressure. The crude product (pale yellow solid) was purified over silica gel chromatography (eluant CH2Cl2/PE 7:3) to afford the product 61 as a white solid (183 mg, 0.41 mmol) in 91% yield. mp=158-162° C.; IR 3057, 3023, 2926, 1494, 1475, 1432, 1376, 1366, 1255, 1182, 1712, 1090, 977, 908, 713, 683 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.48 (d, 1H, J=2.3 Hz, H2), 8.36 (d, 1H, J==8.7 Hz, H8), 8.12 (m, 3H, H4+H7+CHP), 7.67 (s, 1H, H5), 7.56-7.52 (m, 1H, CHP+CHPh), 7.45-7.38 (m, 3H, 3CHP or CHPh), 7.32-7.18 (m, 5H, CHP+CHPh), 3.12-2.97 (m, 4H, 2CH2); 13C NMR (75 MHz, CDCl3) δ 149.2 (C), 145.4 (CH), 141.4 (C), 138.7 (C), 138.1 (C), 137.0 (C), 134.2 (CH), 130.0 (CH), 129.1 (2×CH), 128.6 (2×CH), 128.6 (2×CH), 128.9 (2×CH), 127.6 (CH), 127.5 (C), 126.3 (CH), 122.0 (C), 120.6 (CH), 120.0 (C), 115.1 (CH), 38.2 (CH2), 38.8 (CH2); MS (+ESI) [M+H+]=447.1

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product (pale yellow solid) was purified over silica gel chromatography (eluant CH2Cl2/PE 7:3)

Sources & evidence

ORD record
ord-8780c2c11ea44fdda442b319c41bd878
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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