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Dimethylformamide → N-(5-Cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17321
ノート
印刷プレビュー

反応式

HRID 17321 の反応式
CN(C)C=O.[C:6]([C:8]1[C:13]([CH3:14])=[C:12](I)[C:11]([F:16])=[C:10]([O:17][CH3:18])[C:9]=1[NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])#[N:7].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:6]([C:8]1[C:9]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[C:10]([O:17][CH3:18])[C:11]([F:16])=[C:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]=1[CH3:14])#[N:7]
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 6228DimethylformamideHCID 66827Phenylboronic AcidHCID 86630831N-(2-Cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2-dimethylpropionamide

生成物 1

HCID 86630833N-(5-Cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide収率 96%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

Tetrakis(triphenylphosphine)palladium(0) (1.45 g, 1.26 mmol) was added to an N,N-dimethylformamide (50 ml) suspension of N-(2-cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2-dimethylpropionamide (I-69) (2.45 g, 6.28 mmol), phenylboronic acid (1.15 g, 9.42 mmol), potassium phosphate n-hydrate (74-78%, 3.60 g, 12.6 mmol), followed by stirring at 95° C. for 2 hours. The reaction liquid was cooled, then ethyl acetate (200 ml) was added, followed by washing with saturated brine (50 ml×3), drying over anhydrous magnesium sulfate, concentration under reduced pressure. The residue was purified twice by silica gel column chromatography (chloroform), (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (2.06 g, 96%) as a yellow solid.

後処理

  1. customThe reaction liquid
  2. temperaturewas cooled
  3. washby washing with saturated brine (50 ml×3)
  4. dry with materialdrying over anhydrous magnesium sulfate, concentration under reduced pressure
  5. customThe residue was purified twice by silica gel column chromatography (chloroform), (n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-4704de7340e442bb8f18cb2bbfaee304
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

読み込み中…

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