Cesium fluoride → 4-[5-(1-Methyl-2-pyrrolidinyl)-3-pyridinyl]phenol

HRID 1038

反応式

HRID 1038 の反応式
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([CH:21]3[CH2:25][CH2:24][CH2:23][N:22]3[CH3:26])[CH:18]=[N:19][CH:20]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].[Cs+]>CO>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[C:17]([CH:21]3[CH2:25][CH2:24][CH2:23][N:22]3[CH3:26])[CH:18]=[N:19][CH:20]=2)=[CH:13][CH:14]=1

参加物

4

反応物 2

HCID 25953Cesium fluorideHCID 196943125-(4-Tert-butyldimethylsilyloxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine

生成物 1

HCID 196943114-[5-(1-Methyl-2-pyrrolidinyl)-3-pyridinyl]phenol収率 93%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The above-described pyridine derivative (750 mg, 2.04 mmol) was dissolved in methanol (40 mL) and cesium fluoride (620 mg, 4.08 mmol) was added. The stirred mixture was heated at reflux for 18 h under inert atmosphere. After cooling the solvent was removed in vacuo and the resulting oil was dissolved in ethyl acetate (50 mL). This was washed with water (20 mL), brine (20 mL), dried (MgSO4) and concentrated. The crude material was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:2 ) to 10% methanol: ethyl acetate as eluant to afford 5-(4-hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine 480 mg, 93% as a colorless foam, 1H NMR (CDCl3, 300 MHz): δ 8.66 (d, J=2 Hz, 1 H), 8.43 (d, J=2 Hz, 1 H), 7.90 (s, 1 H), 7.32 (d, J=9 Hz, 2 H), 6.81 (d, J=9 Hz, 2 H), 3.33 (t, J=8 Hz, 1 H), 3.22 (t, J=8 Hz, 1 H), 2.41 (m, 1 H), 2.28 (s, 3 H), 2.10 (m, 2 H), 1.93 (m, 2 H).

後処理

  1. temperatureThe stirred mixture was heated
  2. temperatureat reflux for 18 h under inert atmosphere
  3. temperatureAfter cooling the solvent
  4. customwas removed in vacuo
  5. dissolutionthe resulting oil was dissolved in ethyl acetate (50 mL)
  6. washThis was washed with water (20 mL), brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude material was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:2 ) to 10% methanol

出典と根拠

ORDレコード
ord-3d6034b340a6469bb00e1992fa10c04a
出典データセット
uspto-grants-1998_03
特許番号
US05723477

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