Triethylamine → 5-(5-Cyanopyrid-3-yl)-3-(N-methylpyrrolidin-3-yl)-1H-indole

HRID 1586042ノート

反応式

HRID 1586042 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]1.[C:17]([C:19]1[CH:20]=[C:21]([Sn](C)(C)C)[CH:22]=[N:23][CH:24]=1)#[N:18].C(N(CC)CC)C.[Cl-].[Li+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]([C:19]1[CH:20]=[C:21]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:11]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]2)[CH:22]=[N:23][CH:24]=1)#[N:18]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 153262755-bromo-3-(N-methylpyrrolidin-3-yl)1H-indoleHCID 186990455-(Trimethylstannyl)nicotinonitrile

生成物 1

HCID 154342745-(5-Cyanopyrid-3-yl)-3-(N-methylpyrrolidin-3-yl)-1H-indole収率 11.2%

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒

実験手順

A mixture of 5-bromo-3-(N-methylpyrrolidin-3-yl)-1H-indole (0.500 g, 1.79 mmol), 5-cyano-3-trimethylstannylpyridine (0.525 g, 1.97 mmol, 1.1 eq), bis(triphenylphosphine)palladium(II) chloride (0.628 g, 0.90 mmol, 0.5 eq), triethylamine (1.19 mL, 8.59 mmol, 4.8 eq), lithium chloride (0.235 g, 5.55 mmol, 3.1 eq), and 2,6-di-tert-butyl-4-methylphenol (40 mg) in anhydrous acetontrile (5 mL) was heated at reflux under nitrogen for 20 hours. The resulting reaction mixture was evaporated under reduced pressure, and the residue was column chromatographed using silica gel (approx 50 g) and elution with 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide] to afford the title compound (0.060 g, 0.20 mmol, 11%) as a clear, pale brown oil: LRMS (m/z, relative intensity) 302 (M+, 29), 245 (8), 57 (100); HRMS calculated for C19H18N4 302.1528, found 302.1533.

後処理

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 20 hours
  3. customThe resulting reaction mixture
  4. customwas evaporated under reduced pressure
  5. customchromatographed
  6. washsilica gel (approx 50 g) and elution with 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]

出典と根拠

ORDレコード
ord-acac9c82a5fb4868ad3f9ab9481420a7
出典データセット
uspto-grants-1999_08
特許番号
US05942524

反応ノート

読み込み中…