Cyclopropanecarbonyl chloride → [9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methyl cyclopropanecarboxylate

HRID 992565ノート

反応式

HRID 992565 の反応式
[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([CH2:18][OH:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>C(Cl)Cl.CCOCC>[CH:25]1([C:28]([O:19][CH2:18][C:14]2[N:15]=[CH:16][C:17]3[N:5]([CH2:4][C:3]4[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:2]=4[Cl:1])[C:6]4[C:11]([C:12]=3[CH:13]=2)=[CH:10][CH:9]=[CH:8][CH:7]=4)=[O:29])[CH2:27][CH2:26]1

参加物

5

反応物 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 9928662[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methanol

生成物 1

HCID 9888629[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methyl cyclopropanecarboxylate収率 63.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methanol (357 mg, 1.0 mmol) and cyclopropyl carbonyl chloride (133 mg, 1.27 mmol) in methylene chloride (5 mL) was allowed to stand for 10 minutes. The solvent was evaporated, and the residue partitioned between aqueous Na2CO3 and methylene chloride. The extract was dried over Na2SO4, filtered and evaporated, affording a resin. This was dissolved in ether and filtered through a plug of silica gel, treated with ethereal hydrogen chloride, evaporated, and the residue recrystallized from ethanol/ethyl acetate/ether, affording 270 mg (58%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ8.85 (s, 1H), 8.44 (s, 1 H), 8.25 (d, J=7.9 Hz, 1H), 7.58 (t, J=7.5 Hz, 1H), 7.35-7.28 (m, 3H), 7.10 (dd, J=8, 2.3 Hz, 1H), 6.37 (d, J=2.3 Hz, 1H), 5.62 (s, 2H), 5.46 (s, 2H), 1.74 (m, 2H), 1.56 (m, 1H), 0.84-0.71 (m, 4H); MS (APCI; (M+H)+) m/z 425.

後処理

  1. customThe solvent was evaporated
  2. customthe residue partitioned between aqueous Na2CO3 and methylene chloride
  3. dry with materialThe extract was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customaffording a resin
  7. filtrationfiltered through a plug of silica gel
  8. additiontreated with ethereal hydrogen chloride
  9. customevaporated
  10. customthe residue recrystallized from ethanol/ethyl acetate/ether

出典と根拠

ORDレコード
ord-4fbd52b7aa104e8c92ab80bfb5e682a5
出典データセット
uspto-grants-2002_10
特許番号
US06469021B1

反応ノート

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