Triethylamine → 7-Hydroxy-2-phenyl-4-trimethylsilanylethynyl-thiazolo[4,5-c]pyridine-6 carboxylic acid ethyl ester

HRID 642375ノート

反応式

HRID 642375 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25].C(N(CC)CC)C>O1CCCC1.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>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 866173544-Bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 684262687-Hydroxy-2-phenyl-4-trimethylsilanylethynyl-thiazolo[4,5-c]pyridine-6 carboxylic acid ethyl ester収率 67.2%

試薬・触媒・溶媒 3

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

実験手順

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (636 mg, 1.68 mmole), trimethylsilylacetylene (309 μl, 2.19 mmole), bis(triphenylphosphine)palladium chloride (35 mg, 0.05 mmole), copper(I) iodide (19 mg, 0.10 mmole) and triethylamine (352 μl, 2.52 mmole) in tetrahydrofuran (3.4 ml) was stirred at room temperature for 3.5 h before it was partitioned between ethyl acetate and water, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a gradient of dichloromethane and hexanes to give the title compound as a yellow solid (448 mg). MS: (+) m/z 397.28 (M+1), MS: (−) m/z 395.18 (M−1).

後処理

  1. customwas partitioned between ethyl acetate and water
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a gradient of dichloromethane and hexanes

出典と根拠

ORDレコード
ord-7b53fcbf2e104f03b32e47dbc508c1c4
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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