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Cyclopropylacetylene → 5-Cyclopropylethynyl-3-(dimethylaminomethyleneamino)thiophene-2-carboxylic acid methyl ester

HRID 532458
ノート
印刷プレビュー

反応式

HRID 532458 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Br)=[CH:8][C:9]=1[N:10]=[CH:11][N:12]([CH3:14])[CH3:13])=[O:4].[C:16]([CH:18]1[CH2:20][CH2:19]1)#[CH:17]>C(N(CC)CC)C.C1COCC1.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.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:17]#[C:16][CH:18]2[CH2:20][CH2:19]2)=[CH:8][C:9]=1[N:10]=[CH:11][N:12]([CH3:14])[CH3:13])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 138823CyclopropylacetyleneHCID 600270405-Bromo-3-(dimethylaminomethyleneamino)thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 689443485-Cyclopropylethynyl-3-(dimethylaminomethyleneamino)thiophene-2-carboxylic acid methyl ester

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418476
HCID 178418476、化合物
触媒
HCID 8028Tetrahydrofuran溶媒
HCID 8471Triethylamine溶媒

実験手順

Firstly bis(triphenylphosphine)palladium(II) chloride (602 mg) and then copper(I) iodide (164 mg) were added to a mixture of 5-bromo-3-(dimethylaminomethyleneamino)thiophene-2-carboxylic acid methyl ester (1 g), ethynylcyclopropane (463 mg) in triethylamine (9.5 mL) and THF (4.5 mL). After one hour, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 276.36 (C14H16N2O2S) was obtained in this way; MS (ESI): 277 (M+H+).

後処理

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe crude product was purified by preparative HPLC
  5. customThe product with the molecular weight of 276.36 (C14H16N2O2S) was obtained in this way

出典と根拠

ORDレコード
ord-e65d043a33094806a62df4ce247fbcf9
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08853208B2

反応ノート

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