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Triethylamine → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-(3-hydroxy-1-propynyl)-,ethyl ester

HRID 2377091
ノート
印刷プレビュー

反応式

HRID 2377091 の反応式
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:15](OS(C(F)(F)F)(=O)=O)=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[CH2:31]([O:34][Si](C)(C)C)[C:32]#[CH:33].[Cl-].[Li+].C(N(CC)CC)C>CN(C=O)C.[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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:15]([C:33]#[C:32][CH2:31][OH:34])=[C:10]3[CH:9]=[CH:8]2)=[CH:29][CH:30]=1
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

8

反応物 4

HCID 8471TriethylamineHCID 79696Silane, trimethyl(2-propyn-1-yloxy)-HCID 433294Lithium ChlorideHCID 768529391h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-[[(trifluoromethyl)sulfonyl]oxy]-,ethyl ester

生成物 1

HCID 686643251h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-(3-hydroxy-1-propynyl)-,ethyl ester収率 46%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

To a solution of ethyl 1-(4-fluorobenzyl)-4-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (1.50 g, 3.36 mmol) in DMF (4 mL) was added propargyloxytrimethylsilane (0.73 g, 5.72 mmol), lithium chloride (0.214 g, 5.1 mmol), copper iodide (0.028 g ml, 0.15 mmol), triethylamine (7 ml, 50.4 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.052 g, 0.074 mmol). The resulting mixture was stirred for 20 min at 140° C. in a microwave reactor (Personal Chemistry). The solvent was evaporated and 10 mL ethyl acetate was added. After stirring for 10 min, the mixture was filtered through Celite and the filtrate was concentrated. Purification by flash chromatography (Biotage) over silica gel (1:3, hexane/ethyl acetate) afforded the title product as yellow oil (0.46 g, 46% yield). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 8.69 (s, 1H) 7.36 (d, J=3.28 Hz, 1H) 7.06-7.14 (m, 2H) 6.98-7.06 (m, 2H) 6.84 (d, J=2.53 Hz, 1H) 5.40 (s, 2H) 4.67 (s, 2H) 4.48 (q, J=7.07 Hz, 2H) 1.46 (t, J=7.20 Hz, 3H). LC-MS (APCI, M+H+): 353.1. HPLC: 96% purity.

後処理

  1. customThe solvent was evaporated
  2. addition10 mL ethyl acetate was added
  3. stirringAfter stirring for 10 min
  4. filtrationthe mixture was filtered through Celite
  5. concentrationthe filtrate was concentrated
  6. customPurification by flash chromatography (Biotage) over silica gel (1:3, hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-88d212f6cedc49a3abeae3877b939073
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07468375B2

反応ノート

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