Diisopropylethylamine → 2-Chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde

HRID 468849노트

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HRID 468849 반응식
Br[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([Cl:10])=[N:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[CH:19].C(N(CC)C(C)C)(C)C>O1CCOCC1.C(OCC)(=O)C.[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>[Cl:10][C:5]1[CH:6]=[C:7]([C:2]([C:19]#[C:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])=[CH:3][N:4]=1)[CH:8]=[O:9]

참가 물질

8

반응물 3

HCID 81531DiisopropylethylamineHCID 5859951-Chloro-2-ethynylbenzeneHCID 534183815-Bromo-2-chloropyridine-4-carbaldehyde

생성물 1

HCID 866749492-Chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde수율 88.5%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

A mixture of 5-bromo-2-chloroisonicotinaldehyde (1.0 g, 4.5 mmol), 1-chloro-2-ethynylbenzene (650 mg, 4.7 mmol), N,N-diisopropylethylamine (1.6 mL, 9.1 mmol), copper(I) iodide (43 mg, 0.23 mmol), and bis(triphenylphosphine)palladium(II) chloride (159 mg, 0.23 mmol) in 1,4-dioxane (21 mL) was heated at 50° C. for 1 hour. The cooled reaction mixture was diluted with ethyl acetate (100 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, 40 g, ISCO, 0-30% ethyl acetate in heptane) to afford the title compound as an off-white solid (1.1 g, 88%). 1H NMR (400 MHz, CDCl3) δ 10.64 (s, 1H), 8.77 (s, 1H), 7.77 (s, 1H), 7.62 (dd, J=7.5, 1.7 Hz, 1H), 7.49 (d, J=7.9 Hz, 1H), 7.38 (td, J=7.8, 1.8 Hz, 1H), 7.32 (td, J=7.5, 1.2 Hz, 1H).

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, 40 g, ISCO, 0-30% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-eca51bf2c1d54d6a888d420eb2f326c1
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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