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Potassium Carbonate → (S)-3-{4-[2-(4-Hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester

HRID 2272833
ノート
印刷プレビュー

反応式

HRID 2272833 の反応式
Br[C:2]1[N:28]=[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]3[CH:17]=[CH:16][C:15]([C@@H:18]([C:25]#[C:26][CH3:27])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=3)=[CH:9][N:4]2[N:3]=1.[OH:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C@@H:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[N:4]([N:3]=[C:2]([C:33]4[CH:34]=[CH:35][C:30]([OH:29])=[CH:31][CH:32]=4)[N:28]=3)[CH:9]=2)=[CH:13][CH:14]=1)[C:25]#[C:26][CH3:27])[CH3:24]
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

6

反応物 3

HCID 11430Potassium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 118151365Ethyl (3S)-3-[4-[(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methoxy]phenyl]hex-4-ynoate

生成物 1

HCID 136992561(S)-3-{4-[2-(4-Hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester収率 74.8%

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of ethyl (3S)-3-[4-[(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methoxy]phenyl]hex-4-ynoate (1.0 g, 2.2 mmol) and 4-hydroxy phenyl boronic acid (0.37 g, 2.7 mmol) in 1,4-dioxane (30 mL) is added K2CO3 (0.91 g, 6.6 mmol). The mixture purged with nitrogen for 10 minutes. Pd(PPh3)2Cl2 (0.14 g, 0.2 mmol) is added and the mixture is heated at 100° C. for 12 hours. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth, and washed with EtOAc (2×10 mL). The filtrate is dried over anhydrous sodium sulphate, filtered, and concentrated to dryness. The crude material is purified by silica gel chromatography (combiflash using 24 g redisep column) eluting with 15-20% EtOAc/hexane to give the title compound (0.75 g, 73.52%). LCMS m/z 456.2 (M+H)+.

後処理

  1. customThe mixture purged with nitrogen for 10 minutes
  2. temperatureThe reaction mixture is cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. washwashed with EtOAc (2×10 mL)
  5. dry with materialThe filtrate is dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude material is purified by silica gel chromatography (combiflash using 24 g redisep column)
  9. washeluting with 15-20% EtOAc/hexane

出典と根拠

ORDレコード
ord-134f38ec89bd4b20b5c1687b2cfd9bd1
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09120793B2

反応ノート

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