Water → Tert-butyl 2-(3-cyano-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

HRID 1527307노트

반응식

HRID 1527307 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:3]=1.O.[CH3:21][N:22](C=O)C>[C-]#N.[C-]#N.[Zn+2].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].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:21]([C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:3]=1)#[N:22]

참가 물질

7

반응물 3

HCID 962WaterHCID 6228DimethylformamideHCID 68283706Tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

생성물 1

HCID 68283337Tert-butyl 2-(3-cyano-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

실험 절차

A mixture of tert-butyl 2-(3-iodo-5-methyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate (1.00 g, 2.55 mmol), Zn(CN)2 (329 mg, 2.55 mmol), Pd(dppf)Cl2 (208 mg, 0.25 mmol), Pd2(dba)3 (233 mg, 0.25 mmol), water (2.7 mL) and DMF (20 mL) was subjected to microwave irradiation at 120° C. for 30 min under argon. The reaction mixture was filtered through a pad of Celite and the filtrate was diluted with water and EtOAc. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, then dried (Phase separator) and concentrated under vacuum. The residual oil was purified by flash chromatography on silica gel (EtOAc/c-hexane 1:2 then 1:1). MS (LC/MS): 273.0 [M+H]+; tR (HPLC conditions k): 3.04 min.

후처리

  1. customirradiation at 120° C. for 30 min under argon
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. additionthe filtrate was diluted with water and EtOAc
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. customdried (Phase separator)
  8. concentrationconcentrated under vacuum
  9. customThe residual oil was purified by flash chromatography on silica gel (EtOAc/c-hexane 1:2
  10. custom3.04 min.

출처 및 근거

ORD 기록
ord-00cdaaa646fd4da79986bbc0d32490fa
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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