Triethylamine → HCID 53663791, 화합물

HRID 1585930노트

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HRID 1585930 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 53919960HCID 53919960, 화합물

생성물 1

HCID 53663791HCID 53663791, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-aa86365782934c3483a7fdc56a26b985
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05939439

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