Methanol → tert-Butyl 5-phenylpyridin-2-ylcarbamate

HRID 2221086ノート

反応式

HRID 2221086 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.CO.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[C:18]1([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 162178432-(Boc-amino)-5-bromopyridine

生成物 1

HCID 58671538tert-Butyl 5-phenylpyridin-2-ylcarbamate収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a solution of 1B (7.65 g, 28 mmol) in THF (50 mL)-MeOH (50 mL) at RT was added phenylboronic acid (6.83 g, 56 mmol), PXPd (500 mg, 0.93 mmol), followed by K2CO3 (15.5 g, 112 mmol). The reaction mixture was stirred at 70° C. in a preheated oil bath for 1 h. After this time, the reaction mixture was cooled to RT. The reaction mixture was poured into water (100 mL), and the resultant mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (120 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as an off-white solid (5.4 g, 72%). LC/MS (method A): retention time=3.07 min, (M+H)+=271.

後処理

  1. temperatureAfter this time, the reaction mixture was cooled to RT
  2. extractionthe resultant mixture was extracted with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with saturated NaCl
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel (120 g) column chromatography
  8. washeluting with a gradient of EtOAc (0-60%) in hexane

出典と根拠

ORDレコード
ord-89b5d69a5aa34010b45e5ccad462765b
出典データセット
uspto-grants-2008_05
特許番号
US07368458B2

反応ノート

読み込み中…