Sodium hydride → 5-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine

HRID 1250853ノート

反応式

HRID 1250853 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[CH3:10].Cl[C:13]1[C:22]2[C:17](=[C:18]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[CH2:10][C:13]1[C:22]2[C:17](=[C:18]([O:25][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 118219611-Chloro-5-cyclopentyloxy-6-methoxy-phthalazine

生成物 1

HCID 98659165-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine収率 57.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Under stirring, 55% sodium hydride (3.73 g, 85.56 mmoles) was added to a solution, under nitrogen, of 3,5-dichloro-4-methyl-pyridine (13.86 g, 85.56 mmoles) in anhydrous DMF (100 ml). The mixture was kept under stirring for 1 hour then added with a solution of 1-chloro-5-cyclopentyloxy-6-methoxy-phthalazine (7.95 g, 28.52 mmoles), obtained as described in example 7, in anhydrous dimethylformamide (70 ml). After resting overnight, the mixture was quenched with water, diluted with water and extracted with ethyl acetate. The extract was washed with water and dried on sodium sulphate, then evaporated to dryness. The residue was flash chromatographed (eluent petrolatum/ethyl acetate 1:1) to give 6.58 g of the title compound (yield: 57%).

後処理

  1. stirringunder stirring for 1 hour
  2. customobtained
  3. customthe mixture was quenched with water
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried on sodium sulphate
  8. customevaporated to dryness
  9. customchromatographed (eluent petrolatum/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-00569ee8d4b944d9b7cff0b9d89c3f73
出典データセット
uspto-grants-2002_01
特許番号
US06340684B1

反応ノート

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