(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride) → 8-Propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

HRID 1672102노트

반응식

HRID 1672102 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][C:12]=3[C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1)(=O)=O.[F:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[C:32]([F:35])[C:33]=1[F:34].[OH-].[NH3+]N>O.C1COCC1.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>[CH2:22]([CH:19]1[CH2:18][C:12]2[C:13](=[O:17])[O:14][C:15]3[C:10]([C:11]=2[CH2:21][CH2:20]1)=[CH:9][CH:8]=[C:7]([C:30]1[CH:29]=[C:28]([F:27])[C:33]([F:34])=[C:32]([F:35])[CH:31]=1)[CH:16]=3)[CH2:23][CH3:24]

참가 물질

7

반응물 3

HCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 44558531Aminoammonium hydroxideHCID 579011976-oxo-8-propyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl trifluoromethanesulfonate

생성물 1

HCID 166567888-Propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

10 g (25.6 mmol) of 6-oxo-8-propyl-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-3-yl trifluoromethanesulfonate, 4.50 g (25.6 mmol) of 3,4,5-trifluorobenzeneboronic acid, 10.6 g (38.4 mmol) of sodium metaborate octahydrate, 360 mg (0.51 mmol) of bis(triphenylphosphine)palladium chloride and 50 μl of hydrazinium hydroxide are dissolved in 15 ml of water and 250 ml of THF, and the mixture is refluxed overnight. Water is added to the batch, which is extracted three times with dichloromethane. The combined org. phases are dried over sodium sulfate, the solvent is removed under reduced pressure, and the residue is filtered through silica gel and recrystallised, giving 8-propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one.

후처리

  1. extractionis extracted three times with dichloromethane
  2. dry with materialphases are dried over sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. filtrationthe residue is filtered through silica gel
  5. customrecrystallised

출처 및 근거

ORD 기록
ord-1fbd3b4cb2d047feade059ebf1386e11
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998541B2

반응 노트

불러오는 중…