Sodium Iodide → 7-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)quinolin-2(1H)-one

HRID 1750103ノート

反応式

HRID 1750103 の反応式
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](=[O:16])[NH:13]2)=[CH:8][CH:7]=1.[Na+].[I-].[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:33][CH2:32][CH2:31][N:30](CCCCOC2C=C3C(CCC(=O)N3)=CC=2)[CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+]>CC#N.O>[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:33][CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[C:14]3[C:9]([CH:10]=[CH:11][C:12](=[O:16])[NH:13]3)=[CH:8][CH:7]=2)[CH2:29][CH2:28]1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 299750407-(3-bromopropoxy)quinolin-2(1H)-oneHCID 56597938Unc0006

生成物 1

HCID 565980747-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)quinolin-2(1H)-one収率 39.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of intermediate 32 (217 mg, 0.77 mmol) and NaI (231 mg, 1.54 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 2 (217 mg, 0.77 mmol) and anhydrous K2CO3 (425 mg, 3.08 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred overnight. The reaction solution was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=30:1) to give 7-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)quinolin-2(1H)-one (compound 15) (135 mg, 39%). 1H NMR (300 MHz, CDCl3) δ 11.96 (bs., 1H), 7.72 (d, J=9.3 Hz, 1H) 7.45 (d, J=8.7 Hz, 1H), 7.09-7.07 (m, 2H), 7.01-6.99 (m, 1H), 6.83-6.81 (m, 2H), 6.54 (d, J=9.0 Hz, 1H), 4.15 (t, J=5.7 Hz, 2H), 3.31 (d, J=5.1 Hz, 4H), 2.92-2.96 (m, 4H), 2.76 (t, J=6.6 Hz, 2H), 2.03-1.01 (m, 4H). HPLC: 99%, RT 2.348 min. MS (ESI) m/z 446.1 [M+H]+. mp: 117-118° C.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=30:1)

出典と根拠

ORDレコード
ord-b12996cc42564bfeb8626343064d8b6e
出典データセット
uspto-grants-2015_10
特許番号
US09156822B2

反応ノート

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