Water → HCID 14495336、化合物

HRID 1585934ノート

反応式

HRID 1585934 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.O.[CH3:22][N:23](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([C:22]#[N:23])[CH:5]=1

参加物

6

反応物 3

HCID 962WaterHCID 6228DimethylformamideHCID 53919960HCID 53919960、化合物

生成物 1

HCID 14495336HCID 14495336、化合物

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
100 °C

実験手順

4-Cyano-3-(trifluoromethanesulfonyloxy)-benzoic acid methyl ester (from L-819,063 step 1, 4.92 g, 16 mmol) was dissolved in DMF (22.9 ml) and treated with Zn(CN)2 (1.3 g, 11.2 mmol). The reaction mixture was degassed by bubbling in argon for 1 hr. Pd(PPh3)4 (924 mg, 0.8 mmol) was then added and the reaction was heated to 100° C. for 15 hours. The reaction mixture was poured into water (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was washed with water (2×10 mL), 5% HCl (1×10 mL), brine (1×10 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (100% CH2Cl2) to yield the desired compound. FAB MS: 187 m/z (M+ +H)

後処理

  1. customThe reaction mixture was degassed
  2. customby bubbling in argon for 1 hr
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe organic layer was washed with water (2×10 mL), 5% HCl (1×10 mL), brine (1×10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (100% CH2Cl2)

出典と根拠

ORDレコード
ord-5694c19e02a046e5a410a22d866e60b6
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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