Acetic Acid → HCID 135544009、化合物

HRID 1934502ノート

反応式

HRID 1934502 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:20][C:21]([C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)=O)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=O)[CH:5]=[CH:6][C:7]=1[F:8].CC(O)=O.C[N:33](C)C=O>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:20]=[C:21]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)[N:33]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

4

反応物 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 18679588HCID 18679588、化合物

生成物 1

HCID 135544009HCID 135544009、化合物

反応条件

温度
100 °C

実験手順

A mixture of 3-(3,4-difluorophenyl)-5-(furan-2-yl)-1-(2-hydroxyphenyl)-1,5-pentanedione on Wang resin (2.0 g, 1.76 mmol), NH4OAc (0.80 g), and AcOH (1.0 mL) in dimethylformamide (20 mL) was heated at 100° C. for 18 h. The resin was filtered, and washed with dimethylformamide (×2) and alternating MeOH and CH2Cl2 (×5), and dried under high vacuum overnight. The dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h. After filtration of the reaction mixture, the filtrate was concentrated to dryness. The residue was repeatedly dissolved in CH2Cl2 (10 mL) and concentrated to remove traces of TFA. Purification by flash chromatography gave 2-[4-(3,4-difluoro-phenyl)-6-furan-2-yl-pyridin-2-yl]-phenol; mp 147-148° C.; 1H NMR (DMSO-d6) d 6.78 (m, 1H), 6.98 (m, 2H), 7.37 (m, 1H), 7.43 (m, 1H), 7.67 (m, 1H), 8.00 (m, 2H), 8.15 (d, J=1.3 Hz, 1H), 8.31 (m, 2H), 8.39 (d, J=1.3 Hz, 1H), 14.26, (s, 1H); IR (KBr) 1605 cm−1; MS [M+H]+ m/z=350. Anal. calcd for C21H13F2NO2: C, 72.20; H, 3.75; N, 4.01; Found: C, 71.94; H, 3.62; N, 3.74.

後処理

  1. filtrationThe resin was filtered
  2. washwashed with dimethylformamide (×2)
  3. customdried under high vacuum overnight
  4. additionThe dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h
  5. filtrationAfter filtration of the reaction mixture
  6. concentrationthe filtrate was concentrated to dryness
  7. dissolutionThe residue was repeatedly dissolved in CH2Cl2 (10 mL)
  8. concentrationconcentrated
  9. customto remove traces of TFA
  10. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-a03a9cc2c0ca41619af956892231399d
出典データセット
uspto-grants-2002_05
特許番号
US06384057B1

反応ノート

読み込み中…