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Ethylenediamine → (+/-)-2-(hydroxy(5-methoxy-7-methyl-1H-indol-4-yl)methyl)-1H-indole-6-carbonitrile

HRID 2174094
ノート
印刷プレビュー

反応式

HRID 2174094 の反応式
C(OC([N:8]1[C:16]2[C:11](=[C:12]([CH:20]([C:22]3[N:23](COCC[Si](C)(C)C)[C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[C:26]([C:31]#[N:32])[CH:25]=4)[OH:21])[C:13]([O:18][CH3:19])=[CH:14][C:15]=2[CH3:17])[CH:10]=[CH:9]1)=O)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(N)CN>C1COCC1>[OH:21][CH:20]([C:12]1[C:13]([O:18][CH3:19])=[CH:14][C:15]([CH3:17])=[C:16]2[C:11]=1[CH:10]=[CH:9][NH:8]2)[C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[C:26]([C:31]#[N:32])[CH:25]=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 86701729tert-Butyl-4-((6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

生成物 1

HCID 86701730(+/-)-2-(hydroxy(5-methoxy-7-methyl-1H-indol-4-yl)methyl)-1H-indole-6-carbonitrile

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
65 °C

実験手順

tert-Butyl-4-((6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (70 mg, 0.125 mmol) was dissolved in THF (1.3 mL) and TBAF (1.3 mL, 1.246 mmol) was added. Ethylenediamine (0.084 mL, 1.25 mmol) was then added. The reaction was heated at 65° C. for 4 days. The reaction cooled to room temperature and quenched with saturated aq. ammonium chloride (10 mL) and then diluted with DCM. The layers were separated and the organic layer was washed with water, dried over MgSO4 filtered and concentrated. The resulting residue was absorbed onto silica and purified via flash chromatography (0-75% EtOAc:heptanes) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.39 (s, 1H) 10.80 (s, 1H) 7.66-7.85 (m, 1H) 7.50 (d, J=8.08 Hz, 1H) 7.21 (dd, J=8.15, 1.45 Hz, 1H) 7.14 (t, J=2.78 Hz, 1H) 6.76 (s, 1H) 6.56 (d, J=4.42 Hz, 1H) 6.42 (dd, J=3.03, 2.02 Hz, 1H) 6.07-6.14 (m, 1H) 5.88 (d, J=4.55 Hz, 1H) 3.82 (s, 3H) 2.45 (d, J=0.63 Hz, 3H). MS (ESI−) m/z 330.05 (M−H).

後処理

  1. temperatureThe reaction cooled to room temperature
  2. customquenched with saturated aq. ammonium chloride (10 mL)
  3. additiondiluted with DCM
  4. customThe layers were separated
  5. washthe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was absorbed onto silica
  10. custompurified via flash chromatography (0-75% EtOAc:heptanes)

出典と根拠

ORDレコード
ord-1f2572797a4446f1b1f2a9451608e309
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056874B2

反応ノート

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