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Potassium Carbonate → ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

HRID 2366862
ノート
印刷プレビュー

反応式

HRID 2366862 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:14][CH:15]([O:17][C:18](=[O:43])[NH:19][C@H:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:28]=2)[N:23]([C:39](=[O:41])[CH3:40])[C@@H:22]([CH3:42])[CH2:21]1)[CH3:16].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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].O>[C:39]([N:23]1[C:24]2[C:29](=[CH:28][C:27]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=3)=[CH:26][CH:25]=2)[C@H:20]([NH:19][C:18]([O:17][CH:15]([CH3:16])[CH3:14])=[O:43])[CH2:21][C@@H:22]1[CH3:42])(=[O:41])[CH3:40]
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 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 681853941-Methylethyl [(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

生成物 1

HCID 68185396ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate
収率 59.7%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A flask was charged with ethyl (4-bromophenyl)acetate (0.174 mL, 1.000 mmol), 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Intermediate 52) (416 mg, 1 mmol), potassium carbonate (415 mg, 3.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (73.2 mg, 0.100 mmol) then filled with 1,4-dioxane (6 mL) and water (2 mL) and flushed with nitrogen. The resulting mixture was stirred under microwave irradiation at 120° C. for 30 min then cooled to room temperature. Most of the 1,4-dioxane was removed in vacuo and the residue was partitioned between AcOEt and water. The layers were separated and the aqueous phase was extracted with AcOEt. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 on a 25 G silica cartridge (gradient: 5 to 25% of (10% MeOH in DCM) in DCM) gave ethyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetate (270 mg, 0.597 mmol, 59.7% yield).

後処理

  1. customfor a preparation
  2. customflushed with nitrogen
  3. temperaturethen cooled to room temperature
  4. customMost of the 1,4-dioxane was removed in vacuo
  5. customthe residue was partitioned between AcOEt and water
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with AcOEt
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by SP4 on a 25 G silica cartridge (gradient: 5 to 25% of (10% MeOH in DCM) in DCM)

出典と根拠

ORDレコード
ord-a68860216d5c4b0ea6da6d8d40257a35
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08697725B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート