Sulfoxonium, trimethyl-, iodide (1:1) → 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(tetrahydro-2H-pyran-4-yl)cyclopropyl)thiazolo[5,4-b]pyridine

HRID 1177532노트

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HRID 1177532 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]([CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH2:23])[N:16]=3)=[C:9]([F:30])[CH:8]=1.[I-].[CH3:32][S+](C)(C)=O.CC(C)([O-])C.[K+]>C1COCC1.CS(C)=O>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]2([CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH2:32][CH2:23]2)[N:16]=3)=[C:9]([F:30])[CH:8]=1

참가 물질

6

반응물 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 671121362-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(tetrahydro-2H-pyran-4-yl)vinyl)thiazolo[5,4-b]pyridine

생성물 1

HCID 671118052-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(tetrahydro-2H-pyran-4-yl)cyclopropyl)thiazolo[5,4-b]pyridine

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(tetrahydro-2H-pyran-4-yl)vinyl)thiazolo[5,4-b]pyridine (0.201 g, 0.471 mmol) in 2.5 mL THF was added a solution of trimethylsulfoxonium iodide (0.207 g, 0.943 mmol) and potassium tert-butoxide (0.106 g, 0.943 mmol) in 2.5 mL DMSO. The yellow slurry was sealed and heated to 60° C. After 6 h, the reaction mixture was cooled, quenched with ice and sat'd aq. NH4Cl. The reaction mixture was partitioned between satd aq NH4Cl and DCM. The aqueous layer was extracted with DCM 3 times, and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The material was purified by silica gel chromatography, 0-50% EA/hexanes, to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(tetrahydro-2H-pyran-4-yl)cyclopropyl)thiazolo[5,4-b]pyridine as a solid. MS (ESI) m/z: Calculated: 440.2; Observed: 441.1 (M++1).

후처리

  1. customThe yellow slurry was sealed
  2. temperaturethe reaction mixture was cooled
  3. customquenched with ice
  4. customThe reaction mixture was partitioned between satd aq NH4Cl and DCM
  5. extractionThe aqueous layer was extracted with DCM 3 times
  6. dry with materialthe combined organics were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe material was purified by silica gel chromatography, 0-50% EA/hexanes

출처 및 근거

ORD 기록
ord-becbb258c0cb47ffa138fd19f33ce495
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

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