Triphenylphosphine → Ethyl 2,5-dimethyl-7-[(2,3,6-trifluorobenzyl)oxy]pyrazolo[1,5-a]pyridine-3-carboxylate

HRID 1486241

반응식

HRID 1486241 반응식
[OH:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:16])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]2[CH:5]=[C:4]([CH3:17])[CH:3]=1.[F:18][C:19]1[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:20]=1[CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1COCC1.COC(C)(C)C>[CH3:16][C:9]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]2[CH:5]=[C:4]([CH3:17])[CH:3]=[C:2]([O:1][CH2:21][C:20]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:19]=3[F:18])[N:7]2[N:8]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 1455002,3,6-Trifluorobenzyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 178469270HCID 178469270, 화합물

생성물 1

HCID 117859763Ethyl 2,5-dimethyl-7-[(2,3,6-trifluorobenzyl)oxy]pyrazolo[1,5-a]pyridine-3-carboxylate수율 60.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

실험 절차

1.2 g (5.25 mmol) of ethyl 7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate from Example 8A were dissolved in 48 ml of THF. 1.7 g (10.50 mmol) of 2,3,6-trifluorobenzyl alcohol and 2.9 g (11.03 mmol) of triphenylphosphine were added. Subsequently, 2.2 ml (11.03 mmol) of diisopropyl (E)-diazene-1,2-dicarboxylate were added to the solution, which was stirred at RT for 1 h. 120 ml of tert-butyl methyl ether were added, then the mixture was stirred briefly, and the solids formed were filtered off and dried under high vacuum. 1.2 g of the target compound were obtained (62% of theory).

후처리

  1. stirringthe mixture was stirred briefly
  2. customthe solids formed
  3. filtrationwere filtered off
  4. customdried under high vacuum

출처 및 근거

ORD 기록
ord-46521d68c9e846b49e694be7013db26e
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422285B2

연결된 노트

불러오는 중…