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Toluene → 4-(4'-Methyl-biphenyl-4-ylmethyl)-2-phenyl-morpholine

HRID 737077
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HRID 737077 반응식
Br[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8]2)=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=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(O)C>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:20]=[CH:19][C:5]([CH2:6][N:7]3[CH2:12][CH2:11][O:10][CH:9]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:8]3)=[CH:4][CH:3]=2)=[CH:24][CH:23]=1
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참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 578495044-(4-Bromo-benzyl)-2-phenyl morpholine

생성물 1

HCID 578494924-(4'-Methyl-biphenyl-4-ylmethyl)-2-phenyl-morpholine수율 20%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매

반응 조건

온도
120 °C

실험 절차

91 mg of 4-(4-Bromo-benzyl)-2-phenyl-morpholine was combined with 56 mg of 4-Methylphenyl boronic acid, 16 mg of tetrakis(triphenylphosphine)palladium(0), 0.92 mL of 2M sodium carbonate solution, 2.5 mL toluene and 1.23 mL ethanol. The reaction mixture was heated in a sealed tube at 120° C. overnight in an oil bath. The reaction mixture was filtered through Celite and concentrated in vacuo. The residue was diluted with 4 mL DCM and 130 mg of MP-TsOH resin (4.2 mmol/g loading) was added and the mixture agitated at room temperature overnight. The solution is filtered and the resin is then washed with 2M N3 in methanol to liberate product. The resin is washed several times with methylene chloride, concentrated in vacuo and purified by reverse phase HPLC. 18.5 mg of product was obtained as oil. ES MS m/z 344, 20% yield

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 4 mL DCM and 130 mg of MP-TsOH resin (4.2 mmol/g loading)
  4. additionwas added
  5. filtrationThe solution is filtered
  6. washthe resin is then washed with 2M
  7. washThe resin is washed several times with methylene chloride
  8. concentrationconcentrated in vacuo
  9. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-1495aa064d634c04be80618b38e8383e
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595397B2

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