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

HRID 655263ノート

反応式

HRID 655263 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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+]+.

後処理

  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)

出典と根拠

ORDレコード
ord-54e881a56e0b4cb1a075d2b8ae1404c9
出典データセット
uspto-grants-2011_12
特許番号
US08071581B2

反応ノート

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