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Acetic Acid → N-[3-Fluoro-4-({3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

HRID 2192159
ノート
印刷プレビュー

反応式

HRID 2192159 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[N:4]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:3]=1.[CH3:33][Zn]C.C(O)(=O)C.Cl>O1CCOCC1.C1(C)C=CC=CC=1>[F:22][C:13]1[CH:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[CH:16]=[CH:17][C:12]=1[O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[N:4]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:3]=[C:2]([CH3:33])[C:10]=12
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

7

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 59740993N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamideHCID 178477796HCID 178477796、化合物

生成物 1

HCID 59741018N-[3-Fluoro-4-({3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

100 mg (0.19 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide are dissolved in dioxane (2.5 ml). The solution is degassed and vented with argon. 0.29 ml (0.58 mmol) of a 2M solution of dimethylzinc in toluene and 7.9 mg (0.01 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride/methylene dichloride complex are added, and the mixture is heated at 100° C. for 2.5 hours. The mixture is allowed to cool to RT, acetic acid and 1M hydrochloric acid are added and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

後処理

  1. customThe solution is degassed
  2. temperatureto cool to RT
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by preparative HPLC

出典と根拠

ORDレコード
ord-be1908bbc6444fdd8ba3aa0f3abeda2a
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329716B2

反応ノート

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