Sodium Iodide → 2-[6-bromo-1-(2-chloro-phenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-1-(4-cyclobutyl-piperazin-1-yl)-ethanone

HRID 1713086ノート

反応式

HRID 1713086 の反応式
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[NH:8][CH2:7][CH2:6]2.Cl[CH:21]1[CH2:26][N:25]([CH:27]2[CH2:30][CH2:29][CH2:28]2)[CH2:24][CH2:23][NH:22]1.[C:31](N)(=[O:33])[CH3:32].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[N:8]([CH2:32][C:31]([N:22]1[CH2:23][CH2:24][N:25]([CH:27]3[CH2:30][CH2:29][CH2:28]3)[CH2:26][CH2:21]1)=[O:33])[CH2:7][CH2:6]2

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 668777716-bromo-1-(2-chloro-phenyl)-1,2,3,4-tetrahydroisoquinoline HCl saltHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

生成物 1

HCID 247512302-[6-bromo-1-(2-chloro-phenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-1-(4-cyclobutyl-piperazin-1-yl)-ethanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a stirred suspension of 6-bromo-1-(2-chloro-phenyl)-1,2,3,4-tetrahydroisoquinoline HCl salt (400 mg, 1.11 mmol) in acetonitrile (10.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (241 mg, 1.11 mmol, 1.0 eq.), K2CO3 (306 mg, 2.22 mmol, 2.0 eq.), and NaI (50 mg). The resulting mixture is stirred at rt overnight. Water (10.0 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3), and the combined extracts are dried over sodium sulfate. The solvent is removed under reduced pressure, and the residue is purified through PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.40 (1H, dd), 7.18˜7.32 (5H, m), 6.49 (1H, d), 5.10 (1H, s), 3.81 (1H, m), 3.46 (1H, m), 3.04˜3.40 (6H, m), 2.60˜2.88 (3H, m), 2.41 (1H, m), 2.27 (1H, m), 1.96˜2.14 (4H), 1.60˜1.92 (4H); MS (+VE) m/z 503.9 (M++1).

後処理

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (10 ml×3)
  5. dry with materialthe combined extracts are dried over sodium sulfate
  6. customThe solvent is removed under reduced pressure
  7. customthe residue is purified through PTLC (EtOAc/4% TEA)

出典と根拠

ORDレコード
ord-05d2797dc9ad4a6d8fcac32e3e3a5c32
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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