Triethylamine → Ethyl 3-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)benzoate

HRID 1052074

반응식

HRID 1052074 반응식
Cl.Cl.[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[N:10][CH:11]=2)[CH2:6][CH2:5][NH:4]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(N(CC)CC)C.Br[C:27]1[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:11]1[C:12]2[C:7](=[CH:6][CH:5]=[N:4][CH:3]=2)[CH2:8][CH2:9][N:10]1[C:27]1[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 10796Cesium carbonate2회HCID 90488Ethyl 3-bromobenzoateHCID 634876Binap, (A+-)-HCID 691916791,2,3,4-Tetrahydro-2,7-naphthyridine dihydrochloride

생성물 1

HCID 86695877Ethyl 3-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)benzoate수율 6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

A mixture of 1,2,3,4-tetrahydro-2,7-naphthyridine dihydrochloride (41.4 mg, 0.20 mmol), cesium carbonate (326 mg, 1.0 mmol), and triethylamine (0.056 mL, 0.40 mmol) in 2.0 mL dioxane was warmed until the amine starting material had dissolved. The reaction filtrate was transferred into another reaction vial and the following added: a spatula portion of cesium carbonate, ethyl 3-bromobenzoate (0.032 mL, 0.20 mmol), palladium acetate (2.2 mg, 0.01 mmol) plus catalytic Pd2(dba)3, and RAC-BINAP (6.2 mg, 0.01 mmol). The reaction was heated at 95° C. for 17 hours, filtered, and evaporated to an oil. The oil was chromatograph eluting with CHCl3/EtOAc to give the title compound as a light yellow oil (3.2 mg, 6%). 1H NMR (CDCl3) δ: 8.46 (s, 1H), 8.39 (d, J=5.0 Hz, 1H), 7.66 (dd, J=2.3, 1.5 Hz, 1H), 7.54 (dt, J=7.5, 1.2 Hz, 1H), 7.35 (t, J=7.9 Hz, 1H), 7.16 (dd, J=8.4, 1.9 Hz, 1H), 7.12 (d, J=5.0 Hz, 1H), 4.46 (s, 2H), 4.39 (q, J=7.1 Hz, 2H), 3.62 (t, J=5.9 Hz, 2H), 3.01 (t, J=5.7 Hz, 2H), 1.38-1.44 (m, 3H).

후처리

  1. dissolutionhad dissolved
  2. additionfollowing added
  3. filtrationfiltered
  4. customevaporated to an oil
  5. washeluting with CHCl3/EtOAc

출처 및 근거

ORD 기록
ord-4f0a518933ec41b49abf8c9359f1bbe6
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388176B2

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