Cesium carbonate → 2-azetidin-1-yl-5-bromopyridine

HRID 1173207Notes

Reaction equation

HRID 1173207 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 183298332-azetidin-1-yl-5-bromopyridineYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

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. 1HNMR (CDCl3) δ 8.18 (d, 1H), 7.50 (dd, 1H), 6.18 (d, 1H), 4.03 (t, 4H), 2.40 (q, 2H).

Workup

  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

Sources & evidence

ORD record
ord-b3d0a82787d54955b10f64c899b90ff3
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

Loading…