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Water → HCID 57751037、化合物

HRID 2283311
ノート
印刷プレビュー

反応式

HRID 2283311 の反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][CH:4]=1.Br[C:19]1[CH:20]=[C:21]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([NH2:38])(=[O:37])=[O:36])(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1COCC1.[Cl-].[Na+].O.C(Cl)Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:19]2[CH:20]=[C:21]([S:25]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:36])(=[O:37])[NH2:38])(=[O:26])=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=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

9

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 177505082-Methoxy-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 57751032HCID 57751032、化合物

生成物 1

HCID 57751037HCID 57751037、化合物収率 19%

試薬・触媒・溶媒 4

HCID 178418807
HCID 178418807、化合物
触媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
120 °C

実験手順

1,1′-Bis(diphenylphosphino)ferrocene palladium dichloride methylene chloride adduct (14 mg, 0.02 mmol) was added to a solution of 6-methoxy pyridine-2-boronic acid pinacol ester (135 mg, 0.57 mmol), 2-[(3-bromophenyl)sulfonylamino]benzenesulfonamide (150 mg, 0.38 mmol) (see Example 113a) and Na2CO3 (0.18 mg, 1.72 mmol) in THF:water, 10:1 (4 mL). The reaction mixture was heated in a microwave reactor at 120° C. for 20 min. Some DCM was added followed by brine and the aqueous layer was extracted twice with DCM. The combined organic layers were dried with Na2SO4 and after filtration and evaporation the crude was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (30 mg, 19%) as a yellow oil.

後処理

  1. extractionthe aqueous layer was extracted twice with DCM
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. filtrationafter filtration and evaporation the crude
  4. customwas purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

出典と根拠

ORDレコード
ord-d4a2b1649e4c4b889da0e726262d60ab
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145380B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート