Di-tert-butyl dicarbonate → 6-(2,4-Difluorophenoxy)-3-iodo-4-methyl-5-oxo-4,5-dihydro-pyrazolo[4,3-b]pyridine-1-carboxylic acid tert-butyl ester

HRID 230178노트

반응식

HRID 230178 반응식
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10](=[O:11])[N:9]([CH3:12])[C:8]2[C:13]([I:16])=[N:14][NH:15][C:7]=2[CH:6]=1.[O:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O>O1CCCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.O>[C:26]([O:25][C:23]([N:15]1[C:7]2[CH:6]=[C:5]([O:4][C:3]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:2]=3[F:1])[C:10](=[O:11])[N:9]([CH3:12])[C:8]=2[C:13]([I:16])=[N:14]1)=[O:22])([CH3:29])([CH3:28])[CH3:27]

참가 물질

7

반응물 2

HCID 90495Di-tert-butyl dicarbonateHCID 1784815796-(2,4-Difluorophenoxy)-3-iodo-4-methyl-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

생성물 1

HCID 598128286-(2,4-Difluorophenoxy)-3-iodo-4-methyl-5-oxo-4,5-dihydro-pyrazolo[4,3-b]pyridine-1-carboxylic acid tert-butyl ester수율 120%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-(2,4-difluorophenoxy)-3-iodo-4-methyl-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one (12 mg, 0.0298 mmol) in tetrahydrofuran (5 mL) was added BOC2O (16 mg, 2.5 eq) and DMAP (catalytic). The resulting mixture was heated under reflux for 30 minutes, cooled to room temperature, and diluted with ethyl acetate (35 mL) and water (25 mL). The organic layer was separated, washed successively with water (2×25 mL), 0.5 N HCl (2×20 mL) and brine (1×25 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound as a white powder (18 mg, (M+H)+=504).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customThe organic layer was separated
  4. washwashed successively with water (2×25 mL), 0.5 N HCl (2×20 mL) and brine (1×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7e320f45914346ce90b53cd70ef28ac9
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566708B2

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