Cesium carbonate → tert-butyl 2-(6-fluoro-7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)acetylcarbamate

HRID 1522616노트

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HRID 1522616 반응식
[F:1][C:2]1[C:3]([I:11])=[C:4]2[NH:10][N:9]=[CH:8][C:5]2=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:19][C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:21]>CN(C=O)C>[F:1][C:2]1[CH:7]=[N:6][C:5]2=[CH:8][N:9]([CH2:19][C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[N:10]=[C:4]2[C:3]=1[I:11]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 14221822tert-Butyl (2-chloroacetyl)carbamateHCID 674703846-fluoro-7-iodo-1H-pyrazolo[4,3-b]pyridine

생성물 1

HCID 67469676tert-butyl 2-(6-fluoro-7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)acetylcarbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

To a solution of 6-fluoro-7-iodo-1H-pyrazolo[4,3-b]pyridine (150 mg, 0.570 mmol) in DMF (4 mL) was added Cs2CO3 (279 mg, 0.855 mmol) and tert-butyl 2-chloroacetylcarbamate (121 mg, 0.627 mmol). The mixture was heated at 110° C. for 2 hours. The mixture was then cooled and the reaction was concentrated under vacuum to give a residue. The residue was partitioned between saturated sodium bicarbonate solution and EtOAc (25 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (25 mL). The combined organic layers were, dried over Na2SO4 and evaporated to give tert-butyl 2-(6-fluoro-7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)acetylcarbamate. MS [M+H] found 421.2.

후처리

  1. temperatureThe mixture was then cooled
  2. concentrationthe reaction was concentrated under vacuum
  3. customto give a residue
  4. customThe residue was partitioned between saturated sodium bicarbonate solution and EtOAc (25 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with EtOAc (25 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated

출처 및 근거

ORD 기록
ord-782b0efdc7764024b2a513dcc6d9af61
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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