Dimethylformamide → 4-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid

HRID 1810975ノート

反応式

HRID 1810975 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1.C([O:23][C:24]([N:26]1[CH2:31][CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27]1)=[O:25])(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:29]2[CH2:30][CH2:31][N:26]([C:24]([OH:25])=[O:23])[CH2:27][CH:28]=2)=[C:3]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[CH:4]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 59548898N-(2-bromo-5-chloro-phenyl)-3-chloro-benzamide

生成物 1

HCID 866469174-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid収率 88.8%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

In a 20 mL microwave tube is added N-(2-bromo-5-chloro-phenyl)-3-chloro-benzamide (0.500 g, 1.45 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.532 g, 1.74 mmol), bis(triphenylphosphine) palladium(II) chloride (0.102 g, 0.145 mmol), 2N Na2CO3 aqueous solution (3.62 mL, 7.25 mmol) and DMF (10 mL). The resulting mixture is placed in a microwave oven and heated to 100° C. for 30 min. The reaction turns black. The reaction mixture is poured into water (30 mL) and filtered. The cake is washed with 10 mL water and air dried. The cake is then dissolved in minimum dichloromethane and purified via flash chromatography using 0-30% EtOAc/hexane. The compound comes at 30% EtOAc. Removal of the solvent under vacuum gives 0.504 g of 4-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tent-butyl ester in 78% yield.

後処理

  1. customThe resulting mixture is placed in a microwave oven
  2. filtrationfiltered
  3. washThe cake is washed with 10 mL water and air
  4. customdried
  5. dissolutionThe cake is then dissolved in minimum dichloromethane
  6. custompurified via flash chromatography
  7. customRemoval of the solvent under vacuum

出典と根拠

ORDレコード
ord-b82705cbf4934142b73566fd53d3841b
出典データセット
uspto-grants-2013_01
特許番号
US08362249B2

反応ノート

読み込み中…