Ethyl Acetate → 9-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo(3,4-C)carbazole-1,3(2H,6H)-dione

HRID 11052ノート

反応式

HRID 11052 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:29][CH2:30][CH2:31][OH:32])[C:12]=2[CH:11]=1.C([O-])(=O)C.[K+].C(OCC)(=O)C>[Pd].CO>[OH:28][C:17]1[CH:16]=[CH:15][C:14]2[N:13]([CH2:29][CH2:30][CH2:31][OH:32])[C:12]3[CH:11]=[C:10]([C:3]4[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=4[O:8][CH3:9])[C:22]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=4[C:20]=3[C:19]=2[CH:18]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 517044Potassium AcetateHCID 9981225HCID 9981225、化合物

生成物 1

HCID 103645859-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo(3,4-C)carbazole-1,3(2H,6H)-dione収率 51%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (106) (0.20 g, 0.44 mmol) prepared as described in example 59, potassium acetate (0.20 g) and 5% Pd/C in a solution of ethyl acetate (25 ml) and methanol 1:1 (25 mL) under a atmosphere of hydrogen at 60 psi was reacted for 7 h. The catalyst was filtered off and the filtrate concentrated to dryness. The residue was partitioned between ethyl acetate and water and the organic solution was dried, the drying agent was removed and the solution was concentrated to dryness and chromatographed on silica. Elution with ethyl acetate/petroleum ether (2:1) gave 9-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-methoxyphenyl, R10═CH2CH2CH2OH) (107) in a yield of 51% as an orange powder (from THF/petroleum ether), mp 296–300° C. 1H NMR δ [(CD3)2SO] 10.93 (br s, 1H), 9.31 (br s, 1H), 8.38 (d, J=2.4 Hz, 1H), 7.69 (s, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.42 (m, 1H), 7.35 (dd, J=7.5, 1.7 Hz, 1H), 7.13–7.08 (m, 2H), 7.05 (dd, J=7.2, 7.2 Hz, 1H), 4.62 (t, J=4.8 Hz, 1H), 4.48 (t, J=6.8 Hz, 2H), 3.68 (s, 3H), 3.40 (m, 2H), 1.90 (m, 2H). Found: C, 69.29; H, 4.90; N, 6.54. C24H20N2O5 requires C, 69.22; H, 4.84; N, 6.73.

後処理

  1. customwas reacted for 7 h
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate concentrated to dryness
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic solution was dried
  6. customthe drying agent was removed
  7. concentrationthe solution was concentrated to dryness
  8. customchromatographed on silica
  9. washElution with ethyl acetate/petroleum ether (2:1)

出典と根拠

ORDレコード
ord-fc288b67d39b4f6c88905d219fdffbcc
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

反応ノート

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