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Potassium Carbonate → tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

HRID 1431105
ノート
印刷プレビュー

反応式

HRID 1431105 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:35]2[CH:36]=[CH:37][C:38]([NH2:41])=[N:39][CH:40]=2)O1.C([O-])(O)=O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([C:35]2[CH:40]=[N:39][C:38]([NH2:41])=[CH:37][CH:36]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 59648037tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

生成物 1

HCID 66742367tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate収率 84%

試薬・触媒・溶媒

3
HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

In a 25 mL round-bottomed flask, 3-trifluoromethanesulfonyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (780 mg, 2.46 mmol, Eq: 1.00) was combined with THF (20 ml) to give a colorless solution. The solution was purged with argon for 10 min. Potassium carbonate (1.72 g, 12.3 mmol, Eq: 5.0), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (649 mg, 2.95 mmol, Eq: 1.20), tetrakis(triphenylphosphine)palladium(0) (28.4 mg, 24.6 μmol, Eq: 0.01) and water (200 μl) were added. The reaction mixture was heated to 70° C. and stirred for 16 h. The reaction mixture was poured into saturated NaHCO3 and extracted twice with Et2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 50% (60:10:1 DCM:MeOH:NH4OH)/DCM) to give 3-(6-amino-pyridin-3-yl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (538 mg, 84%). LC/MS-ESI observed [M+H]+ 262.

後処理

  1. customto give a colorless solution
  2. customThe solution was purged with argon for 10 min
  3. extractionextracted twice with Et2O
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 40 g, 50% (60:10:1 DCM:MeOH:NH4OH)/DCM)

出典と根拠

ORDレコード
ord-588d92dc295141dd9b9025e313962529
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08940741B2

反応ノート

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