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

HRID 1054920노트

반응식

HRID 1054920 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

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

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7c3f415a1a4476a966d0098dc98af1a
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394315B2

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