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Dichloromethane → tert-butyl 4-(3-methoxy-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 871849
ノート
印刷プレビュー

反応式

HRID 871849 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.B1([C:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=2)OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C.C(OCC)(=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([C:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]
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

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 117464905-Bromo-2-nitroanisole

生成物 1

HCID 56945492tert-butyl 4-(3-methoxy-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

Argon is bubbled for 10 minutes into a mixture of 4.64 g (20.0 mmol) of the product prepared in step 4.1, 6.25 g (20.2 mmol) of 3,6-dihydro-2H-pyridine-1-N-Boc-4-boronic acid pinacol ester (Frontier Scientific) and 8.29 g (60.0 mmol) of potassium carbonate in 125 mL of anhydrous DMF. 0.98 g (1.2 mmol) of PdCl2dppf.CH2Cl2 is added and the mixture is heated under argon at 90°C. for 3 hours. The resulting mixture is diluted with ethyl acetate and washed twice with water and once with saturated aqueous NaCl. The organic phase is dried over Na2SO4, filtered and concentrated under vacuum. The crude solid obtained is purified by chromatography on a column of silica, eluting with a cyclohexane/ethyl acetate gradient (75/25 to 70/30). 6.02 g of a pale yellow solid are obtained, and are triturated in cyclohexane and then drained by suction and dried in an oven. 5.89 g of the expected product are finally recovered in the form of a white solid. Yield=88%.

後処理

  1. washwashed twice with water and once with saturated aqueous NaCl
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude solid obtained
  6. customis purified by chromatography on a column of silica
  7. washeluting with a cyclohexane/ethyl acetate gradient (75/25 to 70/30)

出典と根拠

ORDレコード
ord-15ed4f1667274f059b946a8f07a3d200
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975250B2

反応ノート

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