Iodoethane → 5-(3-Chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one

HRID 852480

反応式

HRID 852480 の反応式
[CH2:1]([C:3]1[C:4](=[O:12])[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].CN(C)[CH2:20][CH2:21]N(C)C.I[CH2:27][CH3:28].[NH4+].[Cl-:30]>C1COCC1>[Cl:30][C:14]1[CH:15]=[C:16]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4](=[O:12])[C:3]3([CH2:20][CH3:21])[CH2:1][CH3:2])[CH:27]=[CH:28][CH:13]=1

参加物

7

反応物 5

HCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 219862793-Ethylindol-2-oneHCID 178418339Butyllithium

生成物 1

HCID 99482465-(3-Chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-ethylindol-2-one (16 g, 0.1 mol) in dry THF (200 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyllithium (2.5M in hexanes, 80 ml, 0.2 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (30 ml, 0.2 mol). After 30 min. iodoethane (8 ml, 0.1 mol) was added and the reaction mixture was allowed to warm to RT and stirred over night. The reaction mixture was poured into an aqueous NH4Cl solution, extracted with EtOAc (2×) and the combined organic layers were washed with dil. HCl, water, brine, dried (MgSO4) and concentrated. The residual oil was triturated with hexane to afford the title product (9 g, 45%), m.p. 156-159° C.; 1H NMR (DMSO-d6) δ 10.44 (s, 1H), 7.70-7.69 (t, 1H), 7.62-7.59 (m, 1H), 7.58 (d, 1H, J=1.7 Hz), 7.53-7.50 (m, 1H), 7.45-7.41 (t, 1H), 7.36-7.35 (m, 1H), 7.34-7.33 (m, 1H), 6.91-6.89 (d, 1H J=8.2 Hz), 1.87-1.80 (m, 2H), 1.77-1.70 (m, 2H), 0.54-0.50 (t, 6H); MS (+ESI) m/z 190 (M+H).

後処理

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with dil. HCl, water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residual oil was triturated with hexane

出典と根拠

ORDレコード
ord-a3233b57cdc547c8ad1070b2c69ec27d
出典データセット
uspto-grants-2007_08
特許番号
US07253203B2

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