Water → HCID 18677421, 화합물

HRID 380374

반응식

HRID 380374 반응식
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]3[NH:14][C:13]4[CH2:18][CH2:19][N:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][C:12]=4[C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C)C=O>[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]3[N:14]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:13]4[CH2:18][CH2:19][N:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][C:12]=4[C:11]=3[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18677416ethyl 1,3,4,5-tetrahydro-8-(phenylmethoxy)-2H-pyrido[4,3-b]indole-2-carboxylate

생성물 1

HCID 18677421HCID 18677421, 화합물수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
10 °C

실험 절차

A mixture of intermediate (1) (0.09 mol) in N,N-dimethylformamide (200 ml) was stirred at 10° C. under a N2 flow. Sodium hydride (60%; 0.1 mol) was added portionwise. The mixture was stirred for 1 hour at room temperature, then it was cooled to 5° C. Benzylbromide (0.1 mol) was added dropwise. Stirring was continued for 2 hours. The mixture was cooled to 10° C. and poured out into cold water (500 ml). This mixture was extracted with CH2Cl2 (2×250 ml). The separated organic layer was washed with water (100 ml), dried, filtered and the solvent was evaporated. The solid residue was washed with CH3CN (50 ml), cooled and the resulting precipitate was filtered off and dried, yielding 30.0 g (76%) of ethyl 1,3,4,5-tetrahydro-8-(phenyl-methoxy)-5-(phenyl-methyl)-2H-pyrido[4,3-b]indole-2-carboxylate (intermediate 2).

후처리

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. temperatureit was cooled to 5° C
  3. stirringStirring
  4. temperatureThe mixture was cooled to 10° C.
  5. extractionThis mixture was extracted with CH2Cl2 (2×250 ml)
  6. washThe separated organic layer was washed with water (100 ml)
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. washThe solid residue was washed with CH3CN (50 ml)
  11. temperaturecooled
  12. filtrationthe resulting precipitate was filtered off
  13. customdried

출처 및 근거

ORD 기록
ord-efb47c52ba804ed0b99845c8b1b908fe
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303614B1

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