Tributyltin Chloride → (3-Tributylstannyl-pyridin-4-yl)-carbamic acid tert-butyl ester

HRID 8734

反応式

HRID 8734 の反応式
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 99902104-(Boc-amino)pyridineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 69595531(3-Tributylstannyl-pyridin-4-yl)-carbamic acid tert-butyl ester収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Pyridin-4-yl-carbamic acid tert-butyl ester (1.74 g, 8.95 mmol) (prepared as described in Venuti et al, J. Med. Chem. 1988, 31(11), 2136–45) dissolved in THF (150 mL) was cooled to −78° C. and a solution of 1.7M tert-butyllithium in hexanes (11.6 mL, 19.70 mmol) was added dropwise. After the addition, the stirring was continued for 1 h to −78° C. and the solution was then allowed to warm to −20° C. and stirred for an additional 3 h. The reaction was cooled again to −78° C. and tributyltin chloride (2.91 mL, 10.74 mmol) was added dropwise and the reaction was allowed to reach room temperature overnight. A saturated ammonium chloride solution was added and the product extracted with dichloromethane. The combined organics were dried over magnesium sulfate, the solvent was evaporated and residue purified by flash chromatography eluting with 20% ethyl acetate in hexanes to yield 2.12 g of (3-tributylstannyl-pyridin-4-yl)-carbamic acid tert-butyl ester.

後処理

  1. additionAfter the addition
  2. temperatureto warm to −20° C.
  3. temperatureThe reaction was cooled again to −78° C.
  4. waitto reach room temperature overnight
  5. extractionthe product extracted with dichloromethane
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customresidue purified by flash chromatography
  9. washeluting with 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-1fa2eca5f3db433194f7dea595645644
出典データセット
uspto-grants-2006_08
特許番号
US07091200B2

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