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Triethylamine → 8-(3-dimethylamino-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970049
ノート
印刷プレビュー

反応式

HRID 1970049 の反応式
C(N(CC)CC)C.I[C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:19])[C:13]3[NH:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH:10]=1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24].[CH3:28][N:29]([CH3:33])[CH2:30][C:31]#[CH:32]>O1CCOCC1.[Cu](I)I.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>[CH3:28][N:29]([CH3:33])[CH2:30][C:31]#[C:32][C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:19])[C:13]3[NH:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH:10]=1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8471TriethylamineHCID 81643N,N-DimethylpropargylamineHCID 86627515HCID 86627515、化合物

生成物 1

HCID 866275558-(3-dimethylamino-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate収率 36.4%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒
HCID 178418476
HCID 178418476、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

50 mg (0.26 mmol) of copper iodide, 69 mg (0.68 mmol) of triethylamine and 37 mg (0.05 mmol) of dichlorobis(triphenylphosphine)-palladium (11) are added to a suspension of 200 mg (0.52 mmol) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 5 ml of anhydrous dioxan, then this mixture is degassed under argon. After 15 minutes, 65 mg (0.78 mmol) of dimethyl-prop-2-ynyl-amine are added, then the mixture is heated at 100° C. for 6 hours. The raw reaction product is then filtered on celite, the filtrate is evaporated to dryness and the residue is purified by chromatography on silica (ethyl acetate/methanol/ammonia) to give 64 mg (36%) of 8-(3-dimethylamino-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

後処理

  1. customthis mixture is degassed under argon
  2. customThe raw reaction product
  3. filtrationis then filtered on celite
  4. customthe filtrate is evaporated to dryness
  5. customthe residue is purified by chromatography on silica (ethyl acetate/methanol/ammonia)

出典と根拠

ORDレコード
ord-a6952e9ce4a245678f4dea08389851b0
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426437B2

反応ノート

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