4-Bromo-2-nitroaniline → HCID 10353230、化合物

HRID 730233ノート

反応式

HRID 730233 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

HCID 10353230HCID 10353230、化合物収率 119.9%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-71a4331336504c27b746f1b401715061
出典データセット
uspto-grants-2009_09
特許番号
US07582673B2

反応ノート

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