Cesium carbonate → 2-(Azetidin-1-yl)-5-bromopyridine

HRID 1015996노트

반응식

HRID 1015996 반응식
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[Br:6][C:7]1[CH:8]=[CH:9][C:10](F)=[N:11][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:2]1([C:10]2[CH:9]=[CH:8][C:7]([Br:6])=[CH:12][N:11]=2)[CH2:5][CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27831685-Bromo-2-fluoropyridineHCID 12308726Azetidine hydrochloride

생성물 1

HCID 183298332-(Azetidin-1-yl)-5-bromopyridine수율 86%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
95 °C

실험 절차

A mixture of azetidine HCl salt (590 mg, 6.3 mmol), 5-bromo-2-fluoropyridine (1.11 g, 6.3 mmol), Cs2CO3 (4.1 g, 12.6 mmol) and dry DMSO (7 mL) was stirred and heated at 95° C. for 20 h. The reaction mixture was cooled and filtered. The solid was treated with H2O, extracted with CH2Cl2×3. The combined organic layers were dried, filtered to provide 1.15 grams (86%) of desired product as a light yellow solid. MS (M+H)=213.0/215.0. 1H NMR (CDCl3) δ 8.18 (d, 1H), 7.50 (dd, 1H), 6.18 (d, 1H), 4.03 (t, 4H), 2.40 (q, 2H).

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additionThe solid was treated with H2O
  4. extractionextracted with CH2Cl2×3
  5. customThe combined organic layers were dried
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-2141ed7d4349485b81d88466e9c3f92a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985730B2

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