Acetic Acid → HCID 135544009, 화합물

HRID 1934502노트

반응식

HRID 1934502 반응식
[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]

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 18679588HCID 18679588, 화합물

생성물 1

HCID 135544009HCID 135544009, 화합물

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a03a9cc2c0ca41619af956892231399d
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384057B1

반응 노트

불러오는 중…