Sodium Carbonate → tert-butyl 4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate

HRID 1509310노트

반응식

HRID 1509310 반응식
Br[C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1.CC1(C)C(C)(C)OB([C:27]2[CH:41]=[CH:40][C:30]([CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:29][CH:28]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C(=O)(O)[O-].[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].C(Cl)Cl>[O:11]=[C:9]1[CH2:8][O:7][C:6]2[N:12]=[C:2]([C:27]3[CH:41]=[CH:40][C:30]([CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[CH:29][CH:28]=3)[C:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:4][C:5]=2[NH:10]1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 34154424-(tert-Butoxycarbonylaminomethyl)phenylboronic acid, pinacol esterHCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

생성물 1

HCID 67255587tert-butyl 4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate수율 78.1%

시약·촉매·용매 4

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
80 °C

실험 절차

In a reaction tube was added 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (0.19 g, 0.623 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (0.25 g, 0.750 mmol) in 1,4-Dioxane (10 ml), followed by a solution of sodium carbonate (0.198 g, 1.868 mmol) in water (2.5 ml) to give a suspension. This was degassed followed by the addition of PdCl2(dppf)-CH2Cl2 adduct (0.051 g, 0.062 mmol). The resulting mixture was heated at 80° C. for 20 h. The reaction mixture was cooled down to room temperature and diluted with saturated sodium bicarbonate solution (30 ml) and extracted with ethyl acetate (20 mlX3). The combined organic phase was washed with water, brine and concentrated to give product (0.21 g) used for next step without further purification. LCMS (Method D): RT=1.25 min, M+H+=433.2.

후처리

  1. customto give a suspension
  2. customThis was degassed
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. extractionextracted with ethyl acetate (20 mlX3)
  5. washThe combined organic phase was washed with water, brine
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c62d6b3890a34cb1adc4aeb9c3d838ad
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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