Triethylamine → 3-{[(6-Bromopyridin-2-yl)methyl]amino}cyclopent-2-en-1-one

HRID 385785ノート

反応式

HRID 385785 の反応式
Cl.[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18]1(=O)[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[OH-].[Na+].[Cl-].[Na+].O>[Br:2][C:3]1[N:8]=[C:7]([CH2:9][NH:10][C:18]2[CH2:22][CH2:21][C:20](=[O:23])[CH:19]=2)[CH:6]=[CH:5][CH:4]=1

参加物

9

反応物 4

HCID 8471TriethylamineHCID 774661,3-CyclopentanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 45789886(6-Bromopyridin-2-yl)methanamine hydrochloride

生成物 1

HCID 595259943-{[(6-Bromopyridin-2-yl)methyl]amino}cyclopent-2-en-1-one

試薬・触媒・溶媒 4

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
95 °C

実験手順

A solution of 1-(6-bromopyridin-2-yl)methanamine hydrochloride (500 mg, 2.24 mmol) in toluene (10 ml) was charged with triethylamine (0.31 ml, 2.24 mmol). The reaction was stirred for 5 minutes after which cyclopentane-1,3-dione (330 mg, 3.36 mmol) and p-toluenesulfonic acid monohydrate (43 mg, 0.022 mmol) were added. The reaction mixture was heated to reflux at 95° C. for 45 minutes. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (15 ml), 2N sodium hydroxide (10 ml) and brine (10 ml). The layers were separated and the organic layer was then dried over sodium sulfate, filtered and concentrated to yield the title compound.

後処理

  1. additionwere added
  2. temperatureThe reaction mixture was heated
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. customThe layers were separated
  5. dry with materialthe organic layer was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-7685b9c3f3054c099daade80cd204f1a
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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