Potassium Carbonate → 7-Chloro-4-methoxyazaindole

HRID 2423083노트

반응식

HRID 2423083 반응식
[Cl:1][C:2]1[C:3](F)=[C:4]([C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)[CH:5]=O.C(=O)([O-])[O-].[K+].[K+].Cl.CON.O.[NH2:24][NH2:25]>COCCOC>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:4]2[C:3]=1[NH:25][N:24]=[CH:5]2

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 521874O-Methylhydroxylamine hydrochlorideHCID 221397073-Chloro-2-fluoro-6-methoxybenzaldehyde

생성물 1

HCID 534469087-Chloro-4-methoxyazaindole

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
45 °C

실험 절차

To a solution of 3-chloro-2-fluoro-6-(methyloxy)benzaldehyde (10 g, 53.0 mmol) in 1,2-dimethoxyethane (105 mL) was added potassium carbonate (8.06 g, 58.3 mmol) and O-methylhydroxylamine hydrochloride (4.43 g, 53.0 mmol) and the mixture was stirred and heated at 45° C. for 4 hrs. After cooling, the mixture was filtered and concentrated to ˜40 mL and hydrazine monohydrate (58.3 mL, 1856 mmol) was added and the reaction was refluxed under argon over the weekend. The mixture was concentrated to 10-15 mL on the rotary evaporator and then poured into water and stirred for 10 mins. The precipitated solid was collected by filtration and washed with water (3×), sucked dry and then dried in the vacuum oven at 60° C. for 1 hr to give the title compound (D28) as an off white solid (8.83 g)

후처리

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. additionwas added
  4. temperaturethe reaction was refluxed under argon over the weekend
  5. concentrationThe mixture was concentrated to 10-15 mL on the rotary evaporator
  6. additionpoured into water
  7. stirringstirred for 10 mins
  8. filtrationThe precipitated solid was collected by filtration
  9. washwashed with water (3×)
  10. customsucked dry
  11. customdried in the vacuum oven at 60° C. for 1 hr

출처 및 근거

ORD 기록
ord-5fd09a8c372a4aadaf9bed8fd0c24d5b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960563B2

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