1,10-Phenanthroline → 6-(1-phenyl-ethoxy)-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

HRID 1054920ノート

反応式

HRID 1054920 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][CH2:8][N:9]([S:12]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[C:10]=2[N:11]=1.N1[C:35]2[C:26](=[CH:27][CH:28]=[C:29]3[C:34]=2N=CC=C3)[CH:25]=[CH:24]C=1.C([O-])([O-])=[O:37].[Cs+].[Cs+]>[Cu]I>[C:26]1([CH:25]([O:37][C:2]2[CH:3]=[CH:4][C:5]3[O:6][CH2:7][CH2:8][N:9]([S:12]([C:15]4[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=4)(=[O:14])=[O:13])[C:10]=3[N:11]=2)[CH3:24])[CH:35]=[CH:34][CH:29]=[CH:28][CH:27]=1

参加物

5

反応物 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 1180612736-bromo-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

生成物 1

HCID 725442176-(1-phenyl-ethoxy)-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

反応条件

温度
130 °C

実験手順

To 6-bromo-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (50 mg, 140 mmol) in (d,l)-1-phenylethanol (400 μL) was added CuI (15 mg, 79 mmol), 1,10-phenanthroline (15 mg, 83 mmol), and Cs2CO3 (70 mg, 210 mmol). The resulting mixture was heated to 130° C. for 2 hours. Next, the reaction mixture was cooled to room temperature and quenched with a small amount of water, then extracted with ethyl acetate. The aqueous phase was discarded and the organic phase was concentrated under reduced pressure. The resulting residue was purified by HPLC to give 6-(1-phenyl-ethoxy)-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine. LCMS(ESI): calc. C22H22N2O4S=410; obs. M+H=411.

後処理

  1. temperatureNext, the reaction mixture was cooled to room temperature
  2. customquenched with a small amount of water
  3. extractionextracted with ethyl acetate
  4. concentrationthe organic phase was concentrated under reduced pressure
  5. customThe resulting residue was purified by HPLC

出典と根拠

ORDレコード
ord-f7c3f415a1a4476a966d0098dc98af1a
出典データセット
uspto-grants-2016_07
特許番号
US09394315B2

反応ノート

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