HCID 46183928, compound → HCID 46183929, compound

HRID 341305Notes

Reaction equation

HRID 341305 reaction equation
C1(S([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)=O)C=CC=CC=1>C1COCC1>[Cl:31][C:28]1[CH:29]=[N:30][C:11]2[NH:10][C:18]3[C:13]([C:12]=2[CH:27]=1)=[CH:14][C:15]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:16][CH:17]=3

Participants

3

Reactant 1

HCID 46183928HCID 46183928, compound

Product 1

HCID 46183929HCID 46183929, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9-(benzenesulfonyl)-3-chloro-6-(2′-phenylethyl)-9H-pyrido[2,3-b]indole (170 mg, 0.38 mmol, 1 equiv.) in THF (18 ml) under argon TBAF 1M in THF (1.91 ml, 1.91 mmol, 5 equiv.) was added dropwise. The reaction was carried out at reflux for 4 hours and then evaporated. The crude product (brown oil) was purified over silica gel chromatography (eluant AcOEt/PE 1:1) to afford the product R351 as a white solid (108 mg, 0.35 mmol) in 91% yield. mp=216-220° C.; IR 3111, 3028, 2921, 2851, 1600, 1490, 1453, 1389, 1271, 1236, 1087, 1030, 931, 732, 682 cm−1; 1H NMR (300 MHz, DMSO d6) δ 12.31 (br s, 1H, H9), 9.02 (d, 1H, J=2.5 Hz, H2), 8.80 (d, 1H, J=2.4 Hz, H4), 8.48 (s, 1H, H5), 7.85-7.77 (m, 2H, H8+H7), 7.72 (m, 4H, CHPh), 7.61-7.57 (m, 1H, CHPh), 3.46-3.36 (m, 4H, 2CH2); 13C NMR (75 MHz, DMSO d6) δ 150.3 (C), 143.8 (CH), 141.6 (C), 138.2 (C), 133.0 (C), 128.4 (2×CH), 128.3 (CH), 128.2 (2×CH), 127.8 (CH), 125.8 (CH), 121.5 (C), 120.9 (CH), 119.6 (C), 116.3 (C), 111.2 (CH), 37.7 (CH2), 37.3 (CH2); MS (+ESI) [M+H+]=307.2

Workup

  1. temperatureat reflux for 4 hours
  2. customevaporated
  3. customThe crude product (brown oil) was purified over silica gel chromatography (eluant AcOEt/PE 1:1)

Sources & evidence

ORD record
ord-84ccf0dcbec543df8f0a04a844f5438f
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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