Potassium Carbonate → HCID 57912464、化合物

HRID 1971792

反応式

HRID 1971792 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.[CH:20]1([O:24][CH2:25][C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29](B(O)O)=[C:28]([O:37][CH3:38])[CH:27]=2)[CH2:23][CH2:22][CH2:21]1.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.C(OCC)(=O)C.O.COCCOC>[CH:20]1([O:24][CH2:25][C:26]2[CH:27]=[C:28]([O:37][CH3:38])[C:29]([C:2]3[N:3]4[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]4[S:5][CH:6]=3)=[C:30]([O:32][CH3:33])[CH:31]=2)[CH2:23][CH2:22][CH2:21]1

参加物

9

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 57912446{4-[(Cyclobutyloxy)methyl]-2,6-dimethoxyphenyl}boronic acid

生成物 1

HCID 57912464HCID 57912464、化合物収率 89.4%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate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 (987 mg, 2.83 mmol), DME (80 mL) and water (28 mL) were added {4-[(cyclobutyloxy)methyl]-2,6-dimethoxyphenyl}boronic acid (904 mg, 3.4 mmol), potassium carbonate (785 mg, 5.68 mmol), triphenylphosphine (370 mg, 1.42 mmol) and palladium acetate (63.7 mg, 0.282 mmol) in that order, and the mixture was stirred at 90° C. (internal temperature) for 3 hours. Water was added to the reaction 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) to obtain the title compound (1.24 g, 2.53 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 (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-c00b2c3d15a94d3cbcfc301c34f7af67
出典データセット
uspto-grants-2013_04
特許番号
US08431603B2

関連ノート

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