Phosphorus oxychloride → Isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

HRID 647996

반응식

HRID 647996 반응식
CN(C)[C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.P(Cl)(Cl)(Cl)=O.[CH:18]1[CH:19]=[CH:20][N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[C:22]=12.O.O.O.C([O-])(=O)C.[Na+]>O.ClCCCl>[F:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([C:20]2[N:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[C:22]3=[CH:18][CH:19]=2)=[O:11])=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 24813Phosphorus oxychlorideHCID 1410774-fluoro-N,N-dimethylbenzamideHCID 12795102HCID 12795102, 화합물HCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 20484013Isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매2회HCID 962Water용매

실험 절차

A solution of 758 mg. of N,N-dimethyl-4-fluorobenzamide and 0.44 ml. of phosphorous oxychloride in 50 ml. of 1,2-dichloroethane is refluxed for one hour. To this solution is added a solution of 500 mg. of isopropyl 5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in 10 ml. 1,2-dichloroethane. The reaction mixture is refluxed for 3 hours. A solution of 3.3 g. sodium acetate trihydrate in 9 ml water is added and refluxed for a further 10 hours. The organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue is purified by preparative t.l.c. using hexane:ethyl acetate (90:10). Crystallization from dichloromethane-hexane yields isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate (XI, R=H, L=p-F, R2 =iC3H7, n=1), m.p. 92° C.

후처리

  1. additionTo this solution is added a solution of 500 mg
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. temperaturerefluxed for a further 10 hours
  4. customThe organic phase is separated
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue is purified by preparative t.l.c
  9. customCrystallization from dichloromethane-hexane

출처 및 근거

ORD 기록
ord-cc16e4974dda462b8218d8903d8cfca0
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04410534

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