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Sodium Carbonate → 3-(1-(4-(2-Methoxypyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1422655
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HRID 1422655 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:11]3[CH2:16][CH2:15][C:14]([CH2:23][C:24]([CH3:26])=[CH2:25])([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[O:13][C:12]3=[O:27])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][N:31]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH3:28][O:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([N:11]4[CH2:16][CH2:15][C:14]([CH2:23][C:24]([CH3:26])=[CH2:25])([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[O:13][C:12]4=[O:27])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:33]=[CH:32][N:31]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 447548622-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 668695453-(1-(4-Bromophenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

생성물 1

HCID 668695683-(1-(4-(2-Methoxypyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one수율 75%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

3-(1-(4-bromophenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (33 mg, 0.078 mmol), 2-methoxypyridine-4-boronic acid pinacol ester (27 mg, 1.5 equiv), Pd(dppf)Cl2 (6 mg, 10% mol), 2M aq Na2CO3 (1 mL), 1,4-dioxane (2.5 mL) were mixed in a tube for microwave oven. The tube was evacuated and refilled with nitrogen gas (3×) and heated in the microwave oven for 120 min at 130° C. LC-MS found the reaction was complete. The mixture was diluted with EtOAc (10 mL), washed with water (4 mL) and brine (3 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 4-g silica gel column, eluted with a 10˜50% EtOAc in hexanes gradient, to afford 3-(1-(4-(2-methoxypyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (26.5 mg, 75%) as a clear oil.

후처리

  1. customThe tube was evacuated
  2. additionrefilled with nitrogen gas (3×)
  3. additionThe mixture was diluted with EtOAc (10 mL)
  4. washwashed with water (4 mL) and brine (3 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by chromatography on a 4-g silica gel column
  8. washeluted with a 10˜50% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-b34d940d1af94619b44d91a6975d9b09
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927539B2

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