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 2114558ノート

反応式

HRID 2114558 の反応式
[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]

参加物

7

反応物 2

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

生成物 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 ester収率 120%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-72b68bc5d71e4b24a5d2ff2333750a7d
出典データセット
uspto-grants-2008_10
特許番号
US07435731B2

反応ノート

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