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

HRID 1634113노트

반응식

HRID 1634113 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c8484f914fac497da40d1217b4385a87
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506747B1

반응 노트

불러오는 중…