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Triethylamine → tert-Butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate

HRID 541866
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HRID 541866 반응식
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.[C:23]([C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28])#[CH:24]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[NH2:28][C:27]1[CH:26]=[C:25]([C:23]#[C:24][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:6][CH:7]=2)[CH:31]=[CH:30][CH:29]=1
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 11403050tert-Butyl (5-bromopyridin-3-yl)carbamate

생성물 1

HCID 57961935tert-Butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate수율 49%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

Into the reaction flask were added tert-butyl (5-bromopyridin-3-yl)carbamate (2.00 g, 7.32 mmol), copper(I) iodide (56 mg, 0.29 mmol), bis(triphenylphosphine)palladium(II) chloride (0.20 g, 0.29 mmol), tetrahydrofuran (20 mL) and triethylamine (1.1 mL, 8.0 mmol). The reaction mixture was stirred under N2 bubbling for 5 min. 3-Ethynylaniline (0.849 g, 7.3 mmol) was then added. The reaction mixture was heated at 50° C. overnight. After removal of the solvent, the residue was treated with EtOAc and water. The organic layer was dried over Na2SO4 and concentrated under vacuum. The crude was purified by silica gel column chromatography to give the desired product as a yellow gel (0.60 g, 49%). LCMS for C14H12N3O2 ([M-(tBu)+H]+H)+: m/z=254.0.

후처리

  1. customAfter removal of the solvent
  2. additionthe residue was treated with EtOAc and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe crude was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f89739a0ba204327ae8d388cc7d375f5
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871753B2

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