Benzyl Bromide → ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

HRID 915337노트

반응식

HRID 915337 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:3])=[O:2].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH2:24]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

생성물 1

HCID 69231884ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylate수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate (1.0 g, 3.23 mmol) and benzyl bromide (0.60 g, 3.5 mmol) in THF (50 mL) was treated with Cs2CO3 (3.26 g, 10 mmol) and heated to a gentle reflux for 16 h. After cooling to room temperature the reaction was quenched by addition of water and then partitioned between water and EtOAc. The organic phase was dried over MgSO4, and concentrated to yield ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylate as a yellowish solid (1.20 g, 93%): 1H NMR (DMSO-d6) δ 0.93 (t, J=7.0 Hz, 3 H), 4.11 (q, J=7.0 Hz, 2 H), 5.91 (s, 2 H), 7.12 (d, J=8.3 Hz, 2 H), 7.30-7.32 (m, 3 H), 7.50-7.55 (m, 5 H), 7.92 (d, J=9.2 Hz, 1 H), 8.22 (dd, J=9.2, 2.0 Hz, 1 H), 8.34 (d, J=2.0 Hz, 1 H); MS (EI) m/z 400.1 (MH+); Anal. calcd for C24H20N2O4: C, 71.99; H, 5.03; N, 7.00. Found: C, 71.77; H, 5.14; N, 6.71.

후처리

  1. temperatureheated to
  2. temperaturea gentle reflux for 16 h
  3. customwas quenched by addition of water
  4. custompartitioned between water and EtOAc
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1142a737526f4622bc92986076ba1a44
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265148B2

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