Nitrogen → 1-(3,5-Dichloro-4'-fluoro-biphenyl-4-ylmethyl)-3-piperidin-1-yl-pyrrolidin-2-one

HRID 1670842ノート

反応式

HRID 1670842 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.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.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>[Cl:22][C:4]1[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[CH:20]=[C:19]([Cl:21])[C:5]=1[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:8]1=[O:18]

参加物

8

反応物 3

HCID 947NitrogenHCID 2856454-Fluorophenylboronic acidHCID 576580161-(4-Bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one

生成物 1

HCID 576579971-(3,5-Dichloro-4'-fluoro-biphenyl-4-ylmethyl)-3-piperidin-1-yl-pyrrolidin-2-one収率 32.1%

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 (0.150 g, 0.37 mmol) and 4-fluorophenylboronic acid (0.150 g, 1.07 mmol) in toluene (7 mL) and 2M sodium carbonate (1.3 mL) with N2. Treat the reaction with Pd(PPh3)4 (0.043 g, 0.037 mmol) and heat to 90° C. for 4 hours under N2. Cool the reaction, dilute with ethyl acetate, and wash with and water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 0.050 g (32%) of the titled product. Rf=0.46 (9/1 CH2Cl2/methanol). ES MS (m/z): 421 (M+).

後処理

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

出典と根拠

ORDレコード
ord-b9e46ba1905d42c88ba5925495ea42c4
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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