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Binap, (A+-)- → HCID 66700958, 화합물

HRID 1253700
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HRID 1253700 반응식
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[C:19]1[C:28]2[C:23](=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1.CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:32][C:29]([F:30])([F:31])[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[N:22]=[CH:21][CH:20]=[C:19]2[N:8]1[CH2:7][CH2:6][C:5]2([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]2)[CH2:10][CH2:9]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 634876Binap, (A+-)-HCID 212773694-Bromo-8-(trifluoromethyl)quinolineHCID 23676156Sodium t-butoxideHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

생성물 1

HCID 66700958HCID 66700958, 화합물수율 40%

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 1140Toluene용매

실험 절차

A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.5 mmol, 1.0 eq.) and 4-bromo-8-(trifluoromethyl)quinoline (2.5 mmol, 1.0 eq.) and tBuONa (7.5 mmol, 3.0 eq.) in toluene (12 ml) was degassed with argon for 10 min. BINAP (0.15 mmol, 0.06 eq.) and Pd(OAc)2 (0.05 mmol, 0.02 eq.) were added and the reaction mixture obtained was heated under reflux for 14 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order to obtain the desired product. Yield: 40%

후처리

  1. customwas degassed with argon for 10 min
  2. customthe reaction mixture obtained
  3. temperaturewas heated
  4. temperatureunder reflux for 14 h
  5. filtrationThe reaction mixture was filtered over Celite
  6. concentrationthe filtrate was concentrated in vacuo in order
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order

출처 및 근거

ORD 기록
ord-9601748f395e441dbd3c80c3e9a2a858
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08455475B2

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