6-Azaindole → HCID 68244193, 화합물

HRID 588402

반응식

HRID 588402 반응식
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.O=[C:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1.[OH-].[K+]>CO>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:13][CH:12]=2)=[CH:2]1

참가 물질

5

반응물 3

HCID 92196-AzaindoleHCID 14797Potassium HydroxideHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamate

생성물 1

HCID 68244193HCID 68244193, 화합물수율 78%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A suspension of 1H-pyrrolo[2,3-c]pyridine (0.95 g, 8.05 mmol), tert-butyl (4-oxocyclohexyl)carbamate (1.82 g, 8.54 mmol) and KOH (0.95 g, 17.0 mmol) in MeOH (10 mL) was heated at reflux overnight. The solution was added to ice-water (50 mL) and then MeOH (50 mL) was added. The resulting solution was concentrated to circa 50 mL and extracted three times with DCM/MeOH (9:1, 50 mL) and the organic layers were combined and concentrated. The residue was purified by flash chromatography (9:1 DCM/MeOH) to give the title compound as a white solid (1.96 g, 78%). MS (ESI+) m/z=314 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe resulting solution was concentrated to circa 50 mL
  4. extractionextracted three times with DCM/MeOH (9:1, 50 mL)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (9:1 DCM/MeOH)

출처 및 근거

ORD 기록
ord-1694d0eb951a4570abc05c7201d340d8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227967B2

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