4-Methylmorpholine → 4,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamide

HRID 2206672ノート

反応式

HRID 2206672 の反応式
[Br:1][C:2]1[C:10]([C:11](O)=[O:12])=[CH:9][C:8]([Br:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.[CH3:44][NH:45][O:46][CH3:47]>C(Cl)Cl>[Br:1][C:2]1[C:10]([C:11]([N:45]([O:46][CH3:47])[CH3:44])=[O:12])=[CH:9][C:8]([Br:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 710783864,7-dibromo-2,3-dihydro-1H-indene-5-carboxylic acid

生成物 1

HCID 867140174,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamide収率 7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of acid 4 (4.8 g, 15.0 mmol) in CH2Cl2 (80 mL) were added EDCI (3.83 g, 20 mmol), HOBT (2.70 g, 20 mmol), NMM (8.8 mL, 80 mmol) and N,O-dimethylhydroxylamine-HCl (1.95 g, 20 mmol) at rt. The mixture was stirred at rt overnight. The reaction mixture was quenched with water (50 mL) and extracted with DCM (100 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 9 (0.27 g, 0.73 mmol, 7%).

後処理

  1. customThe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with DCM (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-be4fe7e2000b4bdb9a5a8ed9d181d2b3
出典データセット
uspto-grants-2016_06
特許番号
US09371303B2

反応ノート

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