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

HRID 647996

反応式

HRID 647996 の反応式
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

参加物

7

反応物 4

HCID 24813Phosphorus oxychlorideHCID 1410774-fluoro-N,N-dimethylbenzamideHCID 12795102HCID 12795102、化合物HCID 23665404Sodium Acetate Trihydrate

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒2 回HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cc16e4974dda462b8218d8903d8cfca0
出典データセット
uspto-grants-1983_10
特許番号
US04410534

関連ノート

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