Tributylstannane → HCID 68693841, 화합물

HRID 2238440노트

반응식

HRID 2238440 반응식
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

참가 물질

5

반응물 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86620260HCID 86620260, 화합물

생성물 1

HCID 68693841HCID 68693841, 화합물수율 97%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-90bfe7a4efeb4bf7bcbb032ff38cd4da
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

반응 노트

불러오는 중…