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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
ノート
印刷プレビュー

反応式

HRID 1422655 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b34d940d1af94619b44d91a6975d9b09
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927539B2

反応ノート

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