2-Chloro-6-fluorobenzaldehyde → (2-Chloro-6-fluorobenzyl)-[4-(5-cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]amine

HRID 1634113ノート

反応式

HRID 1634113 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]#[N:14])=[CH:11][C:10]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:23]=1[CH:24]=O.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:23]=1[CH2:24][NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]#[N:14])=[CH:11][C:10]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 678472-Chloro-6-fluorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 186771061-(4-Aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole

生成物 1

HCID 18677101(2-Chloro-6-fluorobenzyl)-[4-(5-cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]amine収率 51%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

To a stirred solution of 1-(4-aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole (130 mg, 0.5 mmol) in acetic acid (2 mL) and MeOH (6 mL) at room temperature was added 2-chloro-6-fluorobenzaldehyde (79 mg, 0.5 mmol), followed by sodium cyanoborohydride (79 mg, 1.25 mmol). The reaction mixture was stirred at room temperature for 16 h and then concentrated under a stream of nitrogen. The residue was diluted with water, extracted into ethyl acetate, washed with sodium bicarbonate solution and water, and dried (MgSO4). The residue obtained on concentration was flash chromatographed on silica gel (eluent, gradient of 20-30% EtOAc in CH2Cl2) to provide the title compound (103 mg, 51%). NMR (CDCl3, 400 MHz): 9.1 (s, 1H); 8.7 (br, 1H); 8.3 (d, 1H); 7.6-7.5 (overlapping m, 3H), 7.6-7.5 (overlapping m, 4H), 7.05 (m, 1H); 6.9 (d, 2H), 4.6 (s, 2H).

後処理

  1. concentrationconcentrated under a stream of nitrogen
  2. additionThe residue was diluted with water
  3. extractionextracted into ethyl acetate
  4. washwashed with sodium bicarbonate solution and water
  5. dry with materialdried (MgSO4)
  6. customThe residue obtained on concentration
  7. customchromatographed on silica gel (eluent, gradient of 20-30% EtOAc in CH2Cl2)

出典と根拠

ORDレコード
ord-c8484f914fac497da40d1217b4385a87
出典データセット
uspto-grants-2003_01
特許番号
US06506747B1

反応ノート

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