Nitrogen → HCID 42597520、化合物

HRID 37771

反応式

HRID 37771 の反応式
[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Sn](C)(C)C)=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].Br[C:22]1[C:23]2[C:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=3[CH:35]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.N#N>CN(C=O)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO.C(Cl)Cl>[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:22]2[C:23]3[C:28]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=4[CH:35]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

参加物

9

反応物 4

HCID 947NitrogenHCID 113099-BromophenanthreneHCID 80271Tri-o-tolylphosphineHCID 42597285methyl (2S)-2-acetamido-3-(4-trimethylstannylphenyl)propanoate

生成物 1

HCID 42597520HCID 42597520、化合物収率 59.7%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
70 °C

実験手順

A solution of 95 (259 mg, 0.67 mmol), 9-bromophenanthrene (190 mg, 0.74 mmol), palladium acetate (8 mg, 0.034 mmol), and tri-o-tolylphosphine (20 mg, 0.067 mmol) in DMF (2 mL) was flushed with N2 for 15 min then heated to 70° C. and allowed to stir for 16 h. The reaction was diluted with diethyl ether (20 mL) and washed with water (5×20 mL), dried and evaporated. The crude product was purified by flash column chromatography (15% EtOAc/hexane then 5% MeOH/DCM) to yield the title compound (157 mg, 0.40 mmol, 59%) as a clear oil. [α]D27 +94.6 (c. 0.1, CHCl3). 1H NMR (CDCl3, 300 MHz): δ 8.77 (d, J=9.0 Hz, 1H, ArH4″); 8.71 (d, J=8.1 Hz, 1H, ArH3″); 7.89 (m, 2H, ArH1″ and ArH10″); 7.61 (m, 5H, ArH7″, ArH6″, ArH5″, ArH2″ and ArH1″); 7.48 (d, J=8.4 Hz, 2H, ArH2′ and ArH6′); 7.26 (d, J=8.1 Hz, 2H, ArH3′ and ArH5′); 6.25 (d, J=7.5 Hz, 1H, NH); 5.00 (m, 1H, H2); 3.79 (s, 3H, OCH3); 3.30 (dd, J=5.7, 13.8 Hz, 1H, H3a); 3.20 (dd, J=6.0, 13.8 Hz, 1H, H3b); 2.05 (s, 3H, COCH3). Mass Spectrum (CI, +ve) m/z 398 (100%) [MH+]. HRMS (EI) calcd for C26H23NO3 397.1678, found 397.1680.

後処理

  1. washwashed with water (5×20 mL)
  2. customdried
  3. customevaporated
  4. customThe crude product was purified by flash column chromatography (15% EtOAc/hexane

出典と根拠

ORDレコード
ord-abd913460c6643b4a9fe82d9840fbbec
出典データセット
uspto-grants-2013_09
特許番号
US08524657B2

関連ノート

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