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Sodium Carbonate → 2-Fluoro-4-(5-formyl-pyridin-3-yl)-benzonitrile

HRID 1897778
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HRID 1897778 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[F:12])#[N:2].Br[C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=1)[CH:19]=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=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>[F:12][C:4]1[CH:5]=[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH:19]=[O:20])[CH:21]=2)[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 27847345-Bromo-3-pyridinecarboxaldehyde

생성물 1

HCID 595784372-Fluoro-4-(5-formyl-pyridin-3-yl)-benzonitrile수율 25.1%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 6228
Dimethylformamide
용매

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온도
95 °C

실험 절차

A mixture of 4-cyano-3-fluorophenylboronic acid (0.495 g, 3 mmol), 5-bromonicotinaldehyde (0.558 g, 3.00 mmol), sodium carbonate (2M in water, 3.00 mL, 6.00 mmol), bis(triphenylphosphine)palladium(II) chloride (0.053 g, 0.075 mmol) in DMF (10 mL) was heated to 95° C. for 3 h. After concentration, the residue was dissolved into CH2Cl2-MeOH and mixed with silica gel and concentrated. After flash column (MeOH—CH2Cl2, v/v, 0.5%-1%) yielded a colorless solid (170 mg) ESI-MS m/z: 227 [M+1]+.

후처리

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved into CH2Cl2-MeOH
  3. additionmixed with silica gel
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a096b691ecb94deaa617b9ed4bba17ed
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08519142B2

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