Ammonium Chloride → 8-Fluoro-10,11-dihydro-5-methylene-5H-benzo[4,5]cyclohepta[1,2-b]pyridine

HRID 2218757노트

반응식

HRID 2218757 반응식
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=O)[C:7]3[C:8]([CH2:13][CH2:14][C:4]=2[CH:3]=1)=[N:9][CH:10]=[CH:11][CH:12]=3.[CH3:18][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[CH2:18])[C:7]3[C:8]([CH2:13][CH2:14][C:4]=2[CH:3]=1)=[N:9][CH:10]=[CH:11][CH:12]=3

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 442032048-Fluoro-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-oneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 597699728-Fluoro-10,11-dihydro-5-methylene-5H-benzo[4,5]cyclohepta[1,2-b]pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Chill a mixture of 8-fluoro-10,11-dihydro-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (1.3 g, 5.7 mmol) and dry tetrahydrofuran (50 mL) to 0° C. Treat this mixture with methyl magnesium bromide(3.0M solution in diethyl ether, 5.7 mL, 17.2 mmol). Remove cooling and stir the admixture at room temperature for 15 min. Quench the reaction, while cooling with an ice-water bath, by adding saturated aqueous ammonium chloride solution (50 mL). Separate the layers and extract the aqueous layer with methylene chloride (2×50 mL). Dry the combined organic layers with magnesium sulfate, filter and concentrate to provide the intermediate product as a thick crude oil.

후처리

  1. temperatureChill
  2. customRemove
  3. temperaturecooling
  4. customQuench
  5. customthe reaction
  6. temperaturewhile cooling with an ice-water bath
  7. customSeparate the layers
  8. extractionextract the aqueous layer with methylene chloride (2×50 mL)
  9. dry with materialDry the combined organic layers with magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate
  12. customto provide the intermediate product as a thick crude oil

출처 및 근거

ORD 기록
ord-003e0785793545458001c6d31ffc2406
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07411072B2

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