Trifluoroacetic acid → Methyl 3-chloro-2-[(2-pyrrolidinyl)methoxy]pyridine-5-carboxylate

HRID 350388Notes

Reaction equation

HRID 350388 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2C(OC(C)(C)C)=O)=[N:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=[N:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23511994Methyl 6-((1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methoxy)-5-chloronicotinate

Product 1

HCID 23512234Methyl 3-chloro-2-[(2-pyrrolidinyl)methoxy]pyridine-5-carboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 3-chloro-2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate (235.6 mg, 0.635 mmol) in CH2Cl2 (5.0 mL) was added TFA (1.0 mL) at 0° C., and the reaction mixture was stirred at room temp for 2 hr. The solvent was removed under a reduced pressure. The residue was made basic by the addition of 1N NaOH and extracted with CHCl3. The extract was dried over Na2SO4, concentrated under a reduced pressure to afford 172.3 mg (q.y.) methyl 3-chloro-2-[(2-pyrrolidinyl)methoxy]pyridine-5-carboxylate as a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ 1.55–1.63 (m, 1H), 1.76–1.99 (m, 3H), 2.93–2.99 (m, 1H), 3.02–3.08 (m, 1H), 3.57–3.62 (m, 1H), 3.92 (s, 3H), 4.33 (dd, J=7.3, 10.7 Hz, 1H), 4.44 (dd, J=4.4, 10.7 Hz, 1H), 8.21 (d, J=2.0 Hz, 1H), 8.67 (d, J=2.0 Hz, 1H); MS (FAB) m/z 271 (M++1).

Workup

  1. customThe solvent was removed under a reduced pressure
  2. additionThe residue was made basic by the addition of 1N NaOH
  3. extractionextracted with CHCl3
  4. dry with materialThe extract was dried over Na2SO4
  5. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-307c068ba0d7491e920ef4333c2033f1
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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