Tributylstannane → HCID 68693841、化合物

HRID 2238440ノート

反応式

HRID 2238440 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([N:15]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:14])=[O:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:30]([CH2:38][CH:39]=[CH:40][Cl:41])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Cl:41][CH2:40][CH:39]1[C:2]2[C:11]3[CH:10]=[C:9]([S:12]([N:15]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)(=[O:13])=[O:14])[CH:8]=[CH:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:30]([C:31]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:37])[CH2:38]1

参加物

5

反応物 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86620260HCID 86620260、化合物

生成物 1

HCID 68693841HCID 68693841、化合物収率 97%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 213 (1.00 g, 1.53 mmol), Bu3SnH (550 mg, 1.83 mmol), and AIBN (50 mg, 0.31 mmol) in benzene (25 mL) was heated at reflux for 15 min, then concentrated under reduced pressure. The residue was partitioned between EtOAc and H2O and the EtOAc layer was washed with H2O, brine and dried and evaporated. The residue was purified by chromatography on silica gel, eluting with petroleum ether/EtOAc (9:1) to give tert-butyl 1-(chloromethyl)-8-[(dibenzylamino)sulfonyl]-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (214) (850 mg, 97%). A sample was recrystallised from Et2O/petroleum ether as colorless needles: mp 131-133° C.; 1H NMR (CDCl3) δ 8.30 (br s, 1H), 8.29 (d, J=1.5 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.66 (dd, J=8.6, 1.8 Hz, 1H), 7.23-7.15 (m, 6H), 7.09-7.03 (m, 4H), 4.41 (s, 4H), 4.28 (d, J=11.5 Hz, 1H), 4.15 (dd, J=11.6, 9.0 Hz, 1H), 4.02 (tt, J=9.0, 2.9 Hz, 1 H), 3.75 (dd, J=11.3, 3.5 Hz, 1H), 3.48 (dd, J=11.2, 9.3 Hz, 1H), 1.61 (s, 9H); 13C NMR δ 152.4, 142.7, 138.9, 135.5, 131.3, 130.5, 129.8, 128.9, 128.50, 128.46, 127.7, 124.3, 122.4, 120.3, 118.4, 81.8, 52.7, 50.5, 46.4, 41.4, 28.4. Anal. (C32H33ClN2O4S) C, H, N.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between EtOAc and H2O
  5. washthe EtOAc layer was washed with H2O, brine
  6. customdried
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with petroleum ether/EtOAc (9:1)

出典と根拠

ORDレコード
ord-90bfe7a4efeb4bf7bcbb032ff38cd4da
出典データセット
uspto-grants-2010_05
特許番号
US07718688B2

反応ノート

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