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

HRID 1509310ノート

反応式

HRID 1509310 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c62d6b3890a34cb1adc4aeb9c3d838ad
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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