Potassium Phosphate, Tribasic → Methyl 2-(5-(3,5-difluorophenyl)furo[3,2-b]pyridin-3-yl)acetate

HRID 2176649

反応式

HRID 2176649 の反応式
Cl[C:2]1[N:7]=[C:6]2[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:9][O:10][C:5]2=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([F:31])[CH:30]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[F:24][C:25]1[CH:26]=[C:27]([C:2]2[N:7]=[C:6]3[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:9][O:10][C:5]3=[CH:4][CH:3]=2)[CH:28]=[C:29]([F:31])[CH:30]=1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 10198435Methyl 2-(5-chlorofuro[3,2-b]pyridin-3-yl)acetateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

生成物 1

HCID 57691370Methyl 2-(5-(3,5-difluorophenyl)furo[3,2-b]pyridin-3-yl)acetate収率 83.9%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
100 °C

実験手順

A sealable microwave vial was charged with methyl 2-(5-chlorofuro[3,2-b]pyridin-3-yl)acetate (1.30 g, 5.74 mmol), palladium(II) acetate (0.129 g, 0.574 mmol), potassium phosphate (3.66 g, 17.2 mmol), 3,5-difluorophenylboronic acid (1.81 g, 11.5 mmol), and X-Phos (0.548 g, 1.15 mmol). The vial was sealed, flushed with N2, then dioxane (20 mL) and H2O (2 mL) were added. The solution was sparged with N2 for 10 min, then heated at 100° C. for 24 h. The mixture was then cooled to rt and concentrated for purification by MPLC (Teledine Isco combiFlash Companion). The crude residue was taken up in minimal CH2Cl2 and absorbed onto a 25 g loading cartridge and passed through a Redi-Sep® pre-packed silica gel column (120 g) using 98:2 Hexanes:EtOAc to 70:30 Hexanes:EtOAc gradient to afford methyl 2-(5-(3,5-difluorophenyl)furo[3,2-b]pyridin-3-yl)acetate (1.46 g, 83.8% yield) as a colorless amorphous solid. LRMS (ESI) m/z calcd for C16H12F2NO3 (M+H) 304.1. found 304.2.

後処理

  1. customThe vial was sealed
  2. customflushed with N2
  3. additiondioxane (20 mL) and H2O (2 mL) were added
  4. customThe solution was sparged with N2 for 10 min
  5. temperatureThe mixture was then cooled to rt
  6. concentrationconcentrated for purification by MPLC (Teledine Isco combiFlash Companion)
  7. customabsorbed onto a 25 g loading cartridge

出典と根拠

ORDレコード
ord-11473237ada445948a639b6a0880b065
出典データセット
uspto-grants-2015_06
特許番号
US09066954B2

関連ノート

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