Sodium Carbonate → 4'-Methoxy(1,1'-biphenyl)-3-amine

HRID 240051

반응식

HRID 240051 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:19]=[CH:18][CH:17]=[C:15]([NH2:16])[CH:14]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 201262(4-Methoxyphenyl)boronic acid

생성물 1

HCID 27595634'-Methoxy(1,1'-biphenyl)-3-amine수율 68%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

4-methoxyphenyl boronic acid (0.105 g, 0.693 mmol) and 3-bromoaniline (0.05 mL, 0.462 mmol) were combined in DME (2 mL) in a flame-dried, round-bottom flask. Na2CO3 (2M, 0.485 mL, 0.970 mmol) and Pd(PPh3)4 (0.017 g, 0.014 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum. And the resulting residue was resuspended in H2O and extracted with CH2Cl2. The organic phase was dried over MgSO4 and concentrated under vacuum. The crude product was purified by silica column chromatography (0-20% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.063 g in 68% yield.

후처리

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by silica column chromatography (0-20% EtOAc/hexanes)
  7. customThe purification
  8. customThe solvent was removed under vacuum from fractions
  9. additioncontaining product
  10. customresulting in 0.063 g in 68% yield

출처 및 근거

ORD 기록
ord-5e658e2e96704742b76e89c5b7d4be10
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642788B2

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