Sodium Carbonate → tert-Butyl 4-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate

HRID 1666481ノート

反応式

HRID 1666481 の反応式
Br[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH:17]=1)=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[C:33]1([C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][N:24]=3)[CH:17]=2)=[C:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[CH2:7][CH2:8]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 66876318Tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate

生成物 1

HCID 67445311tert-Butyl 4-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate収率 66%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a solution of tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate (Example 71, Step 2) (91 mg, 0.18 mmol) in anhydrous toluene (3 mL) and ethanol (3 mL) was added phenyl boronic acid (43.7 mg, 0.358 mmol) and 2M Na2CO3 (0.53 mL, 1.08 mmol). This solution was degassed for 20 min and Pd(PPh3)4 (19 mg, 10 mol %) was added. The reaction was heated at 90° C. overnight. The reaction was cooled and extracted with EtOAc (3×). The organic layer was dried over MgSO4 and concentrated. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl2) gave the title compound as a foam (60 mg, 66% yield).

後処理

  1. customThis solution was degassed for 20 min
  2. additionPd(PPh3)4 (19 mg, 10 mol %) was added
  3. temperatureThe reaction was cooled
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customPurification by silica gel column chromatography (0-5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-e25638ca568e49fe9dd281b29250f916
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

読み込み中…