Barium hydroxide, octahydrate → 1-(1-Ethylpropyl)-7-mesityl-4-methyl-1H-pyrrolo[3,2-c]quinoline

HRID 584840ノート

反応式

HRID 584840 の反応式
[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][C:14](I)=[CH:13][C:12]=3[N:11]=[C:10]([C:20]3C(C)=CC(C)=CC=3C)[C:9]=2[CH:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2].[C:29]1([CH3:41])[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[C:30]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COC(OC)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][C:14]([C:30]4[C:31]([CH3:36])=[CH:32][C:33]([CH3:35])=[CH:34][C:29]=4[CH3:41])=[CH:13][C:12]=3[N:11]=[C:10]([CH3:20])[C:9]=2[CH:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2]

参加物

7

反応物 3

HCID 17749109Barium hydroxide, octahydrateHCID 22237855Mesitylboric acidHCID 222497701-(1-ethylpropyl)-7-iodo-4-mesityl-1H-pyrrolo[3,2-c]quinoline

生成物 1

HCID 222496751-(1-Ethylpropyl)-7-mesityl-4-methyl-1H-pyrrolo[3,2-c]quinoline収率 51%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 107951,1-Dimethoxyethane溶媒

実験手順

A solution of 1-(1-ethylpropyl)-7-iodo-4-mesityl-1H-pyrrolo[3,2-c]quinoline (32 mg, 0.09 mmol), mesitylboric acid (17 mg, 0.10 mmol), Pd(PPh3)4 (5 mg, 4.23×10−3 mmol) and barium hydroxide octahydrate (40 mg, 0.13 mmol) in 2,2-dimethoxyethane (6.0 mL) and water (1.0 mL) was stirred at 80 for one day. After filtering through Celite, the filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (17 mg) as white crystals.

後処理

  1. filtrationAfter filtering through Celite
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-747158b051b24bea9d6fc25677590ba4
出典データセット
uspto-grants-2005_08
特許番号
US06927221B2

反応ノート

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