Sodium Carbonate → Ethyl 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoate

HRID 2196752노트

반응식

HRID 2196752 반응식
Br[C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.O.C(O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=2[CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)=[CH:29][CH:28]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 16109102Ethyl 4-(4-(2-Bromobenzyl)piperazin-1-yl)benzoate

생성물 1

HCID 16109105Ethyl 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoate

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매HCID 86587095Dimethoxyethane ethanol water용매

실험 절차

A suspension of EXAMPLE 4B (13.83 g, 34.3 mmol), 4-chlorophenylboronic acid (7.04 g, 45.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.481 g, 0.686 mmol, 2 mol %) and aqueous 2M Na2CO3 (22.5 mL, 45.0 mmol) in dimethoxyethane/H2O/ethanol (7:3:2, 200 mL) was heated at 90° C. for 4.5 hours and diluted with ethyl acetate (200 mL). The layers were separated and the organic phase was dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with a gradient from 5%-40% ethyl acetate/hexanes to give the desired product.

후처리

  1. customThe layers were separated
  2. dry with materialthe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient from 5%-40% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-df6b6f30031443debf106d95d65129c4
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338466B2

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