Dibutyltin dichloride → 5-Bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester

HRID 1190038

반응식

HRID 1190038 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:11])=[CH:8][C:9]=1[NH2:10])=[O:4].[CH3:12][C:13]1([CH3:20])[O:18][CH2:17][C:16](=O)[CH2:15][O:14]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:11])=[CH:8][C:9]=1[NH:10][CH:16]1[CH2:17][O:18][C:13]([CH3:20])([CH3:12])[O:14][CH2:15]1)=[O:4]

참가 물질

7

반응물 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 20158931Methyl 3-amino-5-bromothiophene-2-carboxylate

생성물 1

HCID 577954295-Bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester수율 29.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 3-amino-5-bromo-thiophene-2-carboxylic acid methyl ester (0.5 g, 2.12 mmol) in dry THF (0.6 mL) was treated with 2,2-dimethyl-[1,3]dioxan-5-one (253 μl, 2.12 mmol), followed by dibutyltin dichloride (32 mg, 0.11 mmol). After 5 min phenyl silane (280 μl, 2.27 mmol) was added and the reaction was stirred at room temperature for 3 days. It was dissolved in ethyl acetate (100 mL), washed with NaHCO3 solution and brine. The organic layer was separated, dried over MgSO4, evaporated and left on vacuum pump overnight. The residue was triturated with hexane-ether (4:1) mixture (2×100 mL). The soluble portion was evaporated and purified by chromatography over silica gel (hexane:ethyl acetate—95:5) yielding pure 5-bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester (220 mg, 29%).

후처리

  1. washwashed with NaHCO3 solution and brine
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. waitleft on vacuum pump overnight
  6. customThe residue was triturated with hexane-ether (4:1) mixture (2×100 mL)
  7. customThe soluble portion was evaporated
  8. custompurified by chromatography over silica gel (hexane:ethyl acetate—95:5)

출처 및 근거

ORD 기록
ord-311ec1548b37468e8d19becfae88085f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674118B2

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