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Potassium Acetate → (6-Cyano-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-3-yl)boronic acid

HRID 1846041
ノート
印刷プレビュー

反応式

HRID 1846041 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:10][C:9]=2[O:19][CH3:20])[C:5]([C:21]#[N:22])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[B:28]1(B2OC(C)(C)C(C)(C)O2)[O:32]C(C)(C)C(C)(C)[O:29]1>O1CCOCC1.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[C:21]([C:5]1[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:10][C:9]=2[O:19][CH3:20])=[CH:7][C:2]([B:28]([OH:32])[OH:29])=[CH:3][CH:4]=1)#[N:22]
参加物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 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 867232635-Chloro-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-carbonitrile

生成物 1

HCID 86723224(6-Cyano-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-3-yl)boronic acid収率 25%

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 5-chloro-4′-(ethylsulfonyl)-2′-methoxy-[1,1′-biphenyl]-2-carbonitrile (Preparation 66, 330 mg, 0.985 mmol) in dioxane (5 mL) was added bis(diphenylphosphino)ferrocene-palladium(II)dichloride (30 mg, 0.12 mmol), potassium acetate (290 mg, 2.95 mmol) and bis(pinacolato)diboron (3.75 mg, 1.48 mmol). The reaction was degassed and then placed on a preheated hot plate (100° C.) for 16 hours. The reaction mixture was cooled to room temperature, filtered through celite and the solvent removed in vacuo. The crude material was purified by reverse phase column chromatography eluting with MeCN/H2O to hydrolyse the boronic ester to afford the title compound in 25% yield, 85 mg.

後処理

  1. customThe reaction was degassed
  2. filtrationfiltered through celite
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by reverse phase column chromatography
  5. washeluting with MeCN/H2O

出典と根拠

ORDレコード
ord-0201dd47b48044c99a2f69628ea63781
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952008B2

反応ノート

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