Triethylamine → HCID 53663791、化合物

HRID 1585930ノート

反応式

HRID 1585930 の反応式
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]([C:10]#[N:11])=[CH:8][CH:9]=1)=[O:20]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 53919960HCID 53919960、化合物

生成物 1

HCID 53663791HCID 53663791、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

4-Cyano-3-(trifluoromethanesulfonyloxy)-benzoic acid methyl ester from step 1 (2.5 g, 8.1 mmol) and phenylboronic acid (2 g, 16.2 mmol) were dissolved in DMF (33 ml) and treated with Et3N (3.1 ml, 17.8 mmol). Argon was bubbled into the solution for 20 min. and then a catalytic amount of PdCl2 (PPh3)2 (285 mg, 0.405 mmol) was added. The reaction mixture was warmed to 90° C. and stirred for 3 hours under argon atmosphere. The reaction was quenched with satd. NaHCO3 (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (10% EtOAc/Hexane) to yield the desired product. FAB MS: 238 m/z (M+ +H)

後処理

  1. customArgon was bubbled into the solution for 20 min.
  2. customThe reaction was quenched with satd
  3. extractionNaHCO3 (20 mL) and extracted with EtOAc (2×20 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-aa86365782934c3483a7fdc56a26b985
出典データセット
uspto-grants-1999_08
特許番号
US05939439

反応ノート

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