Nitrogen → 6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-b]pyridine

HRID 655263노트

반응식

HRID 655263 반응식
N#N.Br[C:4]1[CH:5]=[C:6]2[NH:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1.[CH3:13][N:14]1[CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=[N:15]1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][N:14]1[CH:18]=[C:17]([C:4]2[CH:5]=[C:6]3[NH:12][CH:11]=[CH:10][C:7]3=[N:8][CH:9]=2)[CH:16]=[N:15]1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 242292566-Bromo-1H-pyrrolo[3,2-b]pyridine

생성물 1

HCID 687052776-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-b]pyridine수율 61.1%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

To an N2 charged microwave vial, 6-bromo-1H-pyrrolo[3,2-b]pyridine (327 mg, 1.65 mmol) was added and dissolved in DMA (2 mL). The solution was bubbled with N2 for 5 minutes. Next, 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (516 mg, 2.48 mmol) was added to the solution, which was bubbled with N2 for an additional 5 minutes. K2CO3 (320 mg, 2.31 mmol) was dissolved in water (2 ml) and the solution was bubbled with N2 for 5 minutes. The aqueous solution was added to the reaction vessel and the solution was bubbled with N2 again. Finally, the Pd(dppf)2Cl2 (81 mg, 0.10 mmol) was added to the solution, bubbled with N2, sealed and microwaved for 15 minutes at 130° C. The reaction was then transferred to a separatory funnel with dichloromethane (75 mL) and washed with water (2×75 mL). The aqueous layer was back extracted with dichloromethane (75 mL). The organic layers were combined, dried over Na2SO4 and vacuumed down. The crude material was purified by flash chromatography (0-80% acetonitrile/dichloromethane gradient) to afford the title compound (200 mg, 61% yield). MS m/z=199 [M+H+]+.

후처리

  1. customThe solution was bubbled with N2 for 5 minutes
  2. customwas bubbled with N2 for an additional 5 minutes
  3. customthe solution was bubbled with N2 for 5 minutes
  4. additionThe aqueous solution was added to the reaction vessel
  5. customthe solution was bubbled with N2 again
  6. custombubbled with N2
  7. customsealed
  8. custommicrowaved for 15 minutes at 130° C
  9. customThe reaction was then transferred to a separatory funnel with dichloromethane (75 mL)
  10. washwashed with water (2×75 mL)
  11. extractionThe aqueous layer was back extracted with dichloromethane (75 mL)
  12. dry with materialdried over Na2SO4
  13. customThe crude material was purified by flash chromatography (0-80% acetonitrile/dichloromethane gradient)

출처 및 근거

ORD 기록
ord-54e881a56e0b4cb1a075d2b8ae1404c9
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071581B2

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