Nitrogen → 3',5'-Dichloro-4'-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid methyl ester

HRID 1670843ノート

反応式

HRID 1670843 の反応式
Br[C:2]1[CH:20]=[C:19]([Cl:21])[C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH:9]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:8]2=[O:18])=[C:4]([Cl:22])[CH:3]=1.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:26].N#N>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.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>[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:20]=[C:19]([Cl:21])[C:5]([CH2:6][N:7]3[CH2:11][CH2:10][CH:9]([N:12]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)[C:8]3=[O:18])=[C:4]([Cl:22])[CH:3]=2)=[CH:29][CH:28]=1)=[O:26]

参加物

8

反応物 3

HCID 947NitrogenHCID 27343694-Methoxycarbonylphenylboronic acidHCID 576580161-(4-Bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one

生成物 1

HCID 576580003',5'-Dichloro-4'-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid methyl ester収率 39%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
90 °C

実験手順

Purge a mixture of 1-(4-bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one (0.429 g, 1.06 mmol) and 4-methoxycarbonyl phenylboronic acid (0.57 g, 3.16 mmol) in toluene (15 mL) and 2M sodium carbonate (3.7 mL) with N2. Treat the reaction with Pd(PPh3)4 (0.061 g, 0.053 mmol) and heat to 90° C. for 7 hours under N2. Cool the reaction, dilute with ethyl acetate, and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo afford crude product, and purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 0.19 g (39%) of the titled product. Rf=0.40 (9/1 CH2Cl2/methanol). ES MS (m/z): 461 (M+).

後処理

  1. customPurge
  2. additionTreat
  3. temperatureCool
  4. customthe reaction
  5. washwash with water
  6. dry with materialDry the organic layer (Na2SO4)
  7. customremove the solvent in vacuo
  8. customafford crude product
  9. custompurify with a 0 to 10% methanol in CH2Cl2 gradient

出典と根拠

ORDレコード
ord-9c6de28b02c245a9ad8e45e0f7fd1b18
出典データセット
uspto-grants-2011_08
特許番号
US07994176B2

反応ノート

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