4-Bromo-2-nitroaniline → HCID 10353230, 화합물

HRID 730233노트

반응식

HRID 730233 반응식
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1>COCCOC.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>[N+:18]([C:13]1[CH:12]=[C:11]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:16]=[CH:15][C:14]=1[NH2:17])([O-:20])=[O:19]

참가 물질

7

반응물 2

HCID 701324-Bromo-2-nitroanilineHCID 2734379(Pyridin-4-yl)boronic acid

생성물 1

HCID 10353230HCID 10353230, 화합물수율 119.9%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매

실험 절차

To a mixture of pyridine-4-boronic acid (3 mmol), 4-bromo-2-nitrophenylamine (2 mmol), and Pd(PPh3)4 (20 mg) in DME (10 mL), 2 M aqueous Na2CO3 was added. The suspension was then refluxed under nitrogen for 36 h. After cooling to the room temperature, the reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with brine (50 mL), dried over sodium sulfate, and concentrated under vacuum. The residue obtained was purified by column chromatography eluting with hexanes/ethyl acetate (1:1) then ethyl acetate/methanol (10:1) to give 516 mg of 2-nitro-4-pyridin-4-ylphenylamine. 1H NMR (DMSO-d6, 400 MHz): LC: Tr 0.44 min, MS: 216.1 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 7.13 (d, 1H), 7.60 (d, 2H), 7.69 (bs, 2H), 7.88 (dd, 1H), 8.37 (d, 1H), 8.55 (d, 2H) ppm.

후처리

  1. additionwas added
  2. temperatureThe suspension was then refluxed under nitrogen for 36 h
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customwas purified by column chromatography
  8. washeluting with hexanes/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-71a4331336504c27b746f1b401715061
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582673B2

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