Triethylamine → 4-(3-Dimethylamino-prop-1-ynyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29288

反応式

HRID 29288 の反応式
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH3:24][N:25]([CH3:29])[CH2:26][C:27]#[CH:28].C(N(CC)CC)C.CO.ClCCl>C1(C)C=CC=CC=1.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>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:28]#[C:27][CH2:26][N:25]([CH3:29])[CH3:24])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 81643N,N-DimethylpropargylamineHCID 21226129Dichloromethane methanolHCID 865990263-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester2 回

生成物 1

HCID 687118884-(3-Dimethylamino-prop-1-ynyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester収率 65%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

実験手順

To the product of Example 20, Step 1, 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester (900 mg, 2.56 mmol, 1 eq), under nitrogen was added 1-dimethylamino-2-propyne (425 mg, 5.11 mmol, 2 eq), PdCl2(PPh3)2 (90 mg, 0.13 mmol, 0.05 eq), and triethylamine (1.4 mL, 10.23 mmol, 4 eq), in 25 mL of toluene. The reaction mixture was heated at reflux for 16 h until the reaction was complete by TLC. After work up and column chromatography (0-10% MeOH/dichloromethane), 4-(3-dimethylamino-prop-1-ynyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in 65% yield (474 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.4 (t, J=7.1 Hz, 3 H) 2.3 (s, 6 H) 2.8 (s, 3 H) 3.6 (s, 2 H) 4.4 (q, J=7.1 Hz, 2 H) 7.4 (dd, J=7.3, 1.0 Hz, 1 H) 7.5 (m, 1 H) 7.7 (dd, J=8.2, 0.9 Hz, 1 H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h until the reaction

出典と根拠

ORDレコード
ord-1b3be2a316bd44e380a6b69ba25171bd
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

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