Sodium Carbonate → 6-(3-Trifluoromethylphenyl)pyridine-3-carboxaldehyde

HRID 33510

반응식

HRID 33510 반응식
Br[C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>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>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[C:22]([C:2]2[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 117692346-Bromo-3-pyridinecarboxaldehyde

생성물 1

HCID 247297396-(3-Trifluoromethylphenyl)pyridine-3-carboxaldehyde수율 36%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

1.44 g (1.25 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 6-bromo-pyridine-3-carbaldehyde in 60 ml 1,2 dimethoxyethane and stirred for 15 min. 63 ml (125 mmol) of 2 M sodium carbonate solution and 2.5 g (13.16 mmol) of 3-(trifluoromethyl-)-phenylboronic acid were added and the mixture heated to boiling temperature for 18 hours (h). The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.18 g (36%) of 6-(3-Trifluoromethyl-phenyl)-pyridine-3-carbaldehyde

후처리

  1. temperaturethe mixture heated
  2. customfor 18 hours
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. washwashed twice with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated

출처 및 근거

ORD 기록
ord-028251322dd645e88c47ff59cb2644ec
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429605B2

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