Potassium Carbonate → 6-(1-Methylisoquinolin-4-yloxy)nicotinonitrile

HRID 2060856ノート

反応式

HRID 2060856 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=2)=[CH:4][N:3]=1.[CH3:21]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=2)=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 594013876-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

生成物 1

HCID 594012876-(1-Methylisoquinolin-4-yloxy)nicotinonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 6-(1-chloroisoquinolin-4-yloxy)nicotinonitrile (Preparation 17) (300 mg, 1.1 mmol) in DMF (8 mL) under argon was added trimethylboroxine (148 μL, 1.1 mmol) followed by K2CO3 (442 mg, 3.2 mmol) and palladium tetrakistriphenylphosphine (123 mg, 0.1 mmol). The mixture was purged with argon for 5 min and then heated to 80° C. for 16 h. Solvent was removed in vacuo. The residue was partitioned between EtOAc (100 mL) and water (40 mL), the organic phase was washed with water (40 mL), NaHCO3 (40 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (2% MeOH: DCM) to give the title compound: RT=2.40 min; m/z (ES+)=262.4 [M+H]+.

後処理

  1. customThe mixture was purged with argon for 5 min
  2. customSolvent was removed in vacuo
  3. customThe residue was partitioned between EtOAc (100 mL) and water (40 mL)
  4. washthe organic phase was washed with water (40 mL), NaHCO3 (40 mL), brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo
  7. customthe residue purified by column chromatography (2% MeOH: DCM)

出典と根拠

ORDレコード
ord-61ff624063f54ad3a618cb99ab98a386
出典データセット
uspto-grants-2012_10
特許番号
US08278442B2

反応ノート

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