Cesium carbonate → tert-Butyl (2-bromo-5-formylpyridin-4-yl)carbamate

HRID 1502403노트

반응식

HRID 1502403 반응식
[Br:1][C:2]1[CH:9]=[C:8](I)[C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[C:11](=[O:18])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[NH2:12].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:9]=[C:8]([NH:12][C:11](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]([CH:6]=[O:7])=[CH:4][N:3]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 574695636-Bromo-4-iodonicotinaldehyde

생성물 1

HCID 86674965tert-Butyl (2-bromo-5-formylpyridin-4-yl)carbamate수율 40%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

A mixture of 6-bromo-4-iodonicotinaldehyde (50 mg, 0.2 mmol), tert-butyl carbamate (28 mg, 0.24 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (18 mg, 0.03 mmol), palladium acetate (5 mg, 0.02 mmol), and cesium carbonate (100 mg, 0.32 mmol) in 1,4-dioxane (1 mL) was heated at 90° C. for 1 hour. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a white solid (18 mg, 40%). 1H NMR (400 MHz, CDCl3) δ 10.42 (s, 1H), 9.93 (s, 1H), 8.61 (s, 1H), 8.50 (s, 1H), 1.55 (s, 9H).

후처리

  1. customThe cooled reaction mixture
  2. washwashed with water (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-88bbc236eb3243459ae45e0de024fef8
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206175B2

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