Ethylenediamine → N-methyl-N-(3-styryl-1H-indazol-6-yl)-benzene-1,3-diamine

HRID 724378ノート

反応式

HRID 724378 の反応式
[CH3:1][N:2]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:15][N:16]2COCC[Si](C)(C)C)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C(N)CN>>[CH3:1][N:2]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:15][NH:16]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1

参加物

5

反応物 4

HCID 3301EthylenediamineHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 69369951HCID 69369951、化合物

生成物 1

HCID 69370903N-methyl-N-(3-styryl-1H-indazol-6-yl)-benzene-1,3-diamine収率 70.5%

反応条件

温度
70 °C

実験手順

To N-methyl-N-{3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-yl}-benzene-1,3-diamine (237 mg, 0.5 mmol) was added 1M TBAF in THF (10.1 mL, 10.1 mmol), followed by ethylenediamine (0.34 mL, 5.04 mmol, 10 equiv). The resulting mixture was heated to 70° C. for 5 h. The reaction was then quenched with saturated NaHCO3 (10 mL) and extracted 3×35 mL EtOAc. The pooled EtOAc phase was washed 5×20 mL H2O, then brine (20 mL), dried with Na2SO4, decanted and concentrated under reduced pressure to a foam. The crude material was purified by silica gel chromatography (9:1 dichloromethane/ethyl acetate) to give N-methyl-N-(3-styryl-1H-indazol-6-yl)-benzene-1,3-diamine as a foam (120 mg, 70% yield). Rf sm 0.73, Rf p 0.27 (dichloromethane:ethylacetate 7:3); 13C NMR (75 MHz, CDCl3) δ 150.3, 148.8, 147.5, 147.5, 143.9, 143.4, 137.5, 131.1, 130.3, 129.3, 128.9, 128.2, 127.9, 126.7, 121.0, 120.5, 117.0, 116.0, 112.6, 109.8, 109.0, 98.3, 40.7; LCMS (ESI) [M+H]/z Calc'd 341. Found 341. Anal. Calc'd: C, 77.62; H, 5.92; N, 16.46. Found: C, 76.16; H, 5.88; N, 15.95.

後処理

  1. customThe reaction was then quenched with saturated NaHCO3 (10 mL)
  2. extractionextracted 3×35 mL EtOAc
  3. washThe pooled EtOAc phase was washed 5×20 mL H2O
  4. dry with materialbrine (20 mL), dried with Na2SO4
  5. customdecanted
  6. concentrationconcentrated under reduced pressure to a foam
  7. customThe crude material was purified by silica gel chromatography (9:1 dichloromethane/ethyl acetate)

出典と根拠

ORDレコード
ord-ed6d5e30356b495cb3485eece7d99168
出典データセット
uspto-grants-2006_11
特許番号
US07141587B2

反応ノート

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