Water → 2[4-(3-bromopropyl)-3-propylphenyl]-6,7-dihydro-5H-pyrano(2,3-d]thiazole

HRID 603513노트

반응식

HRID 603513 반응식
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][O:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13](O)=[C:12]([CH2:17][CH2:18][CH3:19])[CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:26][CH2:27][CH2:28][CH2:29]Br.O>CN(C=O)C>[Br:26][CH2:27][CH2:28][CH2:29][C:13]1[CH:14]=[CH:15][C:10]([C:2]2[S:1][C:5]3[CH2:6][CH2:7][CH2:8][O:9][C:4]=3[N:3]=2)=[CH:11][C:12]=1[CH2:17][CH2:18][CH3:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 1363400774-(6,7-dihydro-5H-pyrano[2,3-d][1,3]thiazol-2-yl)-2-propylphenol

생성물 1

HCID 670189722[4-(3-bromopropyl)-3-propylphenyl]-6,7-dihydro-5H-pyrano(2,3-d]thiazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(6,7-dihydro-5H-pyrano[2,3-d][1,3]thiazol-2-yl)-2-propylphenol (560 mg, 2.02 mmol) (Example 505) in DMF (5 mL) were added Cs2CO3 (0.99 g, 3.03 mmol) and 1,3-dibromopropane (0.72 mL, 7.07 mmol). The reaction mixture was stirred at rt for 18 h. Water was added, and the aqueous phase was extracted with Et2O. The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (9:1 hexanes/EtOAc) to give the title compound was a white solid (121 mg, 15%). 1H NMR (400 MHz, CDCl3) 7.68 (d, 1H), 7.65 (dd, 1H), 6.82 (d, 1H), 4.30 (t, 2H), 4.12 (t, 2H), 3.62 (t, 2H), 2.78 (t, 2H), 2.61 (t, 2H), 2.34 (quintet, 2H), 2.11-2.03 (m, 2H), 1.63 (hex, 2H), 0.96 (t, 3H); LC-MS: RT=4.05 min, (M+H)+ 396.3.

후처리

  1. extractionthe aqueous phase was extracted with Et2O
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (9:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-7cdff0afec7646ccbe02188b4a91beb3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906653B2

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