Methanol → Methyl 2-isopropenylquinoline-6-carboxylate

HRID 2425566노트

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HRID 2425566 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([CH3:14])=[CH2:13])[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:51][OH:52].CN([CH:56]=[O:57])C>C(OCC)(=O)C.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:51]([O:57][CH3:56])=[O:52])[CH:3]=2)[N:8]=1)([CH3:14])=[CH2:13]

참가 물질

8

반응물 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 666370726-Bromo-2-isopropenylquinoline

생성물 1

HCID 66637151Methyl 2-isopropenylquinoline-6-carboxylate수율 82%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 21584019Toluene ethylacetate용매

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온도
80 °C

실험 절차

A mixture of 6-bromo-2-isopropenylquinoline (200 mg, 1.45 mmol), palladium acetate (18.1 mg, 0.081 mmol), 1,3-bis(diphenylphosphino)propane (33 mg, 0.081 mmol), triethylamine (245 mg, 2.42 mmol. 0.337 ml) and methanol (1.03 g, 1.31 ml 32.2 mmol) in dry DMF (2.5 ml) was heated at 80° C. under carbon monoxide gas (balloon) overnight (15 hours). The mixture was diluted with ethyl acetate-toluene (8:1) (159 ml) and the precipitate was filtered through a pad of celite. The organic layer was washed with water (×2), brine, dried over sodium sulfate and concentrated in vacuo to give the crude product. The crude product was purified by column chromatography on silica gel (150 g) with hexane-ethyl acetate (15:1) to furnish the title compound (150 mg, 82%) as dark yellow solid. 1H NMR (270 MHz, CDCl3) δ 2.36 (3H, s), 3.99 (3H, s), 5.53-5.57 (1H, m), 5.98 (1H, s), 7.73-7.78 (1H, m), 8.08-8.31 (3H, m), 8.54-8.56 (1H, m). MS (ESI): m/z 228.21 [M+H]+.

후처리

  1. filtrationthe precipitate was filtered through a pad of celite
  2. washThe organic layer was washed with water (×2), brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe crude product was purified by column chromatography on silica gel (150 g) with hexane-ethyl acetate (15:1)

출처 및 근거

ORD 기록
ord-beb13d2d47e243da84efd72f448eb746
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964732B2

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