Potassium Carbonate → Tert-butyl[3-(4-cyano-2,6-dimethoxyphenyl)-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate

HRID 1971785ノート

反応式

HRID 1971785 の反応式
Br[C:2]1[N:3]2[N:9]=[C:8]([O:10][CH3:11])[C:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]2[S:5][CH:6]=1.[C:20]([C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25](B(O)O)=[C:24]([O:33][CH3:34])[CH:23]=1)#[N:21].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C.O.COCCOC>[C:15]([O:14][C:13](=[O:19])[NH:12][C:7]1[C:8]([O:10][CH3:11])=[N:9][N:3]2[C:2]([C:25]3[C:24]([O:33][CH3:34])=[CH:23][C:22]([C:20]#[N:21])=[CH:27][C:26]=3[O:28][CH3:29])=[CH:6][S:5][C:4]=12)([CH3:18])([CH3:17])[CH3:16]

参加物

10

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 57912433(3-Bromo-6-methoxy-pyrazolo[5,1-b]thiazol-7-yl)-carbamic acid tert-butyl esterHCID 588166494-Cyano-2,6-dimethoxyphenylboronic acid

生成物 1

HCID 44478735Tert-butyl[3-(4-cyano-2,6-dimethoxyphenyl)-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate収率 51.7%

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒HCID 21899848Ethylacetate heptane溶媒

反応条件

温度
90 °C

実験手順

To a mixture of tert-butyl (3-bromo-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate (461 mg, 1.33 mmol), DME (49 mL) and water (16 mL) were added (4-cyano-2,6-dimethoxyphenyl)boronic acid (412 mg, 2.00 mmol), potassium carbonate (366 mg, 2.66 mmol), triphenylphosphine (174 mg, 0.659 mmol) and palladium acetate (29.8 mg, 0.132 mmol) in that order, and the mixture was stirred at 90° C. (internal temperature) for 2 hours. Water was added to the mixture, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1 then 1/1) to obtain the title compound (296 mg, 0.688 mmol).

後処理

  1. stirringAfter thoroughly shaking the mixture
  2. customthe organic layer was separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. distillationthe solvent in the filtrate was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (
  8. additionmixture of n-heptane and ethyl acetate

出典と根拠

ORDレコード
ord-27290163f36f4e06baf6d91a43d803f0
出典データセット
uspto-grants-2013_04
特許番号
US08431603B2

反応ノート

読み込み中…