Diisopropylamine → HCID 68953726、化合物

HRID 2384911ノート

反応式

HRID 2384911 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:8][C:9]=1Br)=[O:4].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(NC(C)C)(C)C>CN(C=O)C.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.CCOCC>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:8][C:9]=1[C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[O:4]

参加物

9

反応物 4

HCID 7912DiisopropylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 689498673-Bromo-5-(4-chloro-phenyl)-thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 68953726HCID 68953726、化合物収率 57.3%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

React 3-bromo-5-(4-chloro-phenyl)-thiophene-2-carboxylic acid methyl ester (0.66 g, 2.0 mmol) with (trimethylsilyl)acetylene (216 mg, 2.2 mmol), Pd(PPh3)2Cl2 (140 mg, 0.20 mmol), CuI (38.2 mg, 0.20 mmol), PPh3 (210 mg, 0.80 mmol) and diisopropyl amine (3.3 mL, 30 mmol) in DMF (1.0 mL) at 120° C. for 30 min in a microwave reactor. Treat the mixture with Et2O (15 mL), filter, pour into 0.1 M HCl (15 mL), and extract with Et2O (3×10 mL). Wash the combined organic layers with saturated NaHCO3 (20 mL) and water (20 mL). Purify the crude material by chromatography, eluting with 30% CH2Cl2/hexane to give 400 mg (57%) of the title compound. LC-MS/ES m/z (35Cl) 349.0 [M+H]+.

後処理

  1. filtrationfilter
  2. additionpour into 0.1 M HCl (15 mL)
  3. extractionextract with Et2O (3×10 mL)
  4. washWash the combined organic layers with saturated NaHCO3 (20 mL) and water (20 mL)
  5. customPurify the crude material by chromatography
  6. washeluting with 30% CH2Cl2/hexane

出典と根拠

ORDレコード
ord-aa1d3fe9f1ff464fa6a3eb25bd687d8a
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

読み込み中…