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

HRID 338762

反応式

HRID 338762 の反応式
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]

参加物

9

反応物 5

HCID 8471TriethylamineHCID 10796Cesium carbonate2 回HCID 90488Ethyl 3-bromobenzoateHCID 634876Binap, (A+-)-HCID 691916791,2,3,4-Tetrahydro-2,7-naphthyridine dihydrochloride

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f34261a1613642e4bfa0a977490a886d
出典データセット
uspto-grants-2014_11
特許番号
US08889870B2

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