Triphenyl phosphite → HCID 58324498, 화합물

HRID 1645050노트

반응식

HRID 1645050 반응식
C[O:2][C:3]([C:5]1[N:6]([C:10]2[C:19]([N+:20]([O-])=O)=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)=O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[O:2]=[C:3]1[NH:20][C:19]2[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[N:11][C:10]=2[N:6]2[CH:7]=[CH:8][CH:9]=[C:5]12

참가 물질

6

반응물 2

HCID 7540Triphenyl phosphiteHCID 58324515methyl 6-(2-(methoxycarbonyl)-1H-pyrrol-1-yl)-5-nitronicotinate

생성물 1

HCID 58324498HCID 58324498, 화합물수율 54%

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 516859Ammonium metavanadate촉매HCID 6344Dichloromethane용매

실험 절차

Methyl 6-(2-(methoxycarbonyl)-1H-pyrrol-1-yl)-5-nitronicotinate (5.00 g, 16.38 mmol) was dissolved in dichloromethane (Volume: 82 ml) and to this solution was added triphenyl phosphite (0.051 g, 0.164 mmol), ammonium metavanadate (0.115 g, 0.983 mmol) and Pt/C (5% wt.) (0.639 g, 0.164 mmol). The reaction mixture was hydrogenated at 100 psi at 25° C. for 36 h. The reaction mixture was filtered through a short plug of celite and the plug and precipitate were washed well with methanol (100 mL) and then MeOH:DCM (100 mL, 1:1). The solids (celite and Pt/C) were continuously extracted with Me0H/DCM mixture (1:1) in a Soxlet extractor for 2 d. The extracts were combined with the earlier filtrates, concentrated in vacuo, crystallized with MeOH (100 mL) and the resulting solid was filtered off and suspended in ethyl ether (200 mL). The solid were filtered off and dried in vacuum to afford methyl 6-oxo-5,6-dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine-3-carboxylate (2.15 g, 8.84 mmol, 54.0% yield) as a grey solid. 1H NMR (DMSO-d6) δ 11.49 (s, 1H), 8.69 (s, 1H), 8.15 (br. s., 1H), 8.11 (s, 1H), 7.16 (d, J=2.5 Hz, 1H), 6.78 (t, J=3.0 Hz, 1H), 3.91 (s, 3H). [M+H] calc'd for C12H9N3O3, 244; found, 244.

후처리

  1. filtrationThe reaction mixture was filtered through a short plug of celite
  2. washthe plug and precipitate were washed well with methanol (100 mL)
  3. extractionThe solids (celite and Pt/C) were continuously extracted with Me0H/DCM mixture (1:1) in a Soxlet extractor for 2 d
  4. concentrationconcentrated in vacuo
  5. customcrystallized with MeOH (100 mL)
  6. filtrationthe resulting solid was filtered off
  7. filtrationThe solid were filtered off
  8. customdried in vacuum

출처 및 근거

ORD 기록
ord-09d049113f7f46efbcf19323887dc2a0
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124606B2

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