Water → HCID 67100256, 화합물

HRID 1868804노트

반응식

HRID 1868804 반응식
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](Cl)[CH:10]=2)[C:5]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[C:4](=[O:17])[C:3]=1[C:18]([NH:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+].O.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:10]=2)[C:5]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[C:4](=[O:17])[C:3]=1[C:18]([NH:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19]

참가 물질

9

반응물 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67099598HCID 67099598, 화합물

생성물 1

HCID 67100256HCID 67100256, 화합물수율 41.7%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

To 1,1-dimethylethyl N-((4′-hydroxy-2′-oxo-6′-chloro-spiro[cyclopentane-1,1′-naphthalen]-3′-yl)carbonyl)glycinate (250 mg, 616 μmol, Example 25A-B) and phenylboronic acid (113 mg, 924 μmol) were added 1,4-dioxane (3080 μL) and K2CO3 in water (924 μL, 1848 μmol). The reaction was then flushed with nitrogen for 10 minutes. Pd2(dba)3 (56.4 mg, 61.6 μmol) and X-Phos (58.7 mg, 123 μmol) were then added, and the reaction mixture was stirred at 110° C. for 6 hours. The reaction mixture was diluted with 75 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (115 mg) as an oil after preparatory LC. MS (m/z)=392(M+H-tBu)+.

후처리

  1. customThe reaction was then flushed with nitrogen for 10 minutes
  2. additionadded to a separatory funnel
  3. custompartitioned with NaHCO3 (saturated, aqueous)
  4. washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7dc8eb59da0f44c496f237ee6b08ce20
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635715B2

반응 노트

불러오는 중…