Potassium Iodide → HCID 59837421、化合物

HRID 272931ノート

反応式

HRID 272931 の反応式
BrCCCOC1C=CC(C2(C#[N:19])CCCCC2)=CC=1.Cl[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2([C:37]#[N:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+].[CH3:47][O:48][CH2:49][C@H:50]1[CH2:54][CH2:53][CH2:52][NH:51]1>CN1C(=O)CCC1>[NH3:19].[CH3:47][O:48][CH2:49][C@H:50]1[CH2:54][CH2:53][CH2:52][N:51]1[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2([C:37]#[N:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1

参加物

8

反応物 5

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 23091704HCID 23091704、化合物HCID 598375041-[4-(3-Bromo-propoxy)-phenyl]-cyclohexanecarbonitrile

生成物 2

HCID 222AmmoniaHCID 59837421HCID 59837421、化合物収率 54%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
75 °C

実験手順

A (1:3) mixture of 1-[4-(3-bromo-propoxy)-phenyl]-cyclohexanecarbonitrile and 1-[4-(3-chloro-propoxy)-phenyl]-cyclohexanecarbonitrile (2.00 g, 7.20 mmol), Cs2CO3 (2.58 g, 7.20 mmol), potassium iodide (0.20 g, 1.20 mmol) and (R)-(−)-2-(methoxymethyl)pyrrolidine (1.07 mL, 8.60 mmol) in NMP (20 mL) was heated to 75° C. overnight. The reaction mixture was cooled to ambient temperature, concentrated in vacuo, and quenched by adding water (30 mL). The crude product was extracted with ethyl acetate (30×mL) and the organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, 100:0:0 to 90:10:1 to give the title compound as a brown oil (1.39 g, 54%). 1H NMR (400 MHz, CDCl3) δ 7.38 (d, 2H), 6.70 (d, 2H), 4.02 (t, 2H), 3.46-3.38 (m, 1H), 3.36-3.28 (m, 3H), 3.24-3.16 (m, 1H), 3.12-3.04 (m, 1H), 2.72-2.58 (m, 1H), 2.52-2.44 (m, 1H), 2.30-2.20 (m, 1H), 2.18-2.06 (m, 2H), 1.98 (pentet, 2H), 1.92-1.60 (m, 12H), 1.36-1.18 (m, 1H); HRMS (ESI+) 357.2537 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customquenched
  4. additionby adding water (30 mL)
  5. extractionThe crude product was extracted with ethyl acetate (30×mL)
  6. dry with materialthe organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe compound was purified by column chromatography on Biotage® silica gel
  10. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-439af9c4efb94e9586d82a556bc5af98
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

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