Cesium fluoride → 3-[3-[2-(Benzyloxy)ethyl]phenyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine

HRID 2095333ノート

反応式

HRID 2095333 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([Sn](C)(C)C)[CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([O:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36](I)[CH:35]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[F-].[Cs+]>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH2:24]([O:31][CH2:32][CH2:33][C:34]1[CH:35]=[C:36]([C:18]2[CH:17]=[N:16][CH:15]=[C:14]([O:13][CH2:12][C@@H:9]3[CH2:10][CH2:11][N:8]3[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:19]=2)[CH:37]=[CH:38][CH:39]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

7

反応物 3

HCID 25953Cesium fluorideHCID 105744715-Iodo-A-85380, 5-trimethylstannyl N-boc derivativeHCID 593713811-[2-(Benzyloxy)ethyl]-3-iodobenzene

生成物 1

HCID 593714993-[3-[2-(Benzyloxy)ethyl]phenyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine収率 58.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

3-[[1-(tert-Butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (619 mg, 1.45 mmol), 1-[2-(benzyloxy)ethyl]-3-iodobenzene (490 mg, 1.45 mmol), and anhydrous DMF (5.0 mL) were placed in a 25 mL round-bottom flask with magnetic stirrer. To this mixture were rapidly added CsF (441 mg, 2.90 mmol, 2.0 equiv.), CuI (27.5 mg, 0.14 mmol, 0.10 equiv.), and Pd(PPh3)4 (84 mg, 0.07 mmol, 0.05 equiv.). The flask was fitted with a three-way stopcock with nitrogen balloon, and the atmosphere was exchanged three times. The reaction mixture was heated at 50° C. for 5 h. TLC analysis of the crude reaction mixture indicated that the aryl iodide was absent. After evaporation of the solvent in vacuo, the residue was chromatographed on silica gel with EtOAc/petroleum ether/Et3N 2:4:0.05 to give the title compound (400 mg, 58%) as a colorless oil. LC-MS (ESI) m/z 475 (M+H+).

後処理

  1. customThe flask was fitted with a three-way stopcock with nitrogen balloon
  2. customTLC analysis of the crude reaction mixture
  3. customAfter evaporation of the solvent in vacuo
  4. customthe residue was chromatographed on silica gel with EtOAc/petroleum ether/Et3N 2:4:0.05

出典と根拠

ORDレコード
ord-457e1bc0a80e4f199eb8628ceef3f3a3
出典データセット
uspto-grants-2013_05
特許番号
US08445684B2

反応ノート

読み込み中…