Trifluoroacetic acid → 5-(Pent-4-ynyloxy)-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine

HRID 1666510Notes

Reaction equation

HRID 1666510 reaction equation
[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:15]=[C:16]([CH:31]=[CH:32][CH:33]=2)[CH:17]=[C:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)=[N:11][CH:12]=1)[CH2:2][CH2:3][C:4]#[CH:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:33]=[CH:32][CH:31]=[C:16]([CH:17]=[C:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:15]=2)=[N:11][CH:12]=1)[CH2:2][CH2:3][C:4]#[CH:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86623921HCID 86623921, compound

Product 1

HCID 866239225-(Pent-4-ynyloxy)-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridineYield 114.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-(pent-4-ynyloxy)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.68 g, 1.33 mmol) in dry CH2Cl2 (3 mL) cooled to 0° C. was added TFA (1 mL, 13.3 mmol) dropwise. The mixture was stirred for 30 min. The reaction was concentrated and then partitioned between saturated NaHCO3 solution and CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (0.53 g, 99%). m/z (421.2, MH+).

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between saturated NaHCO3 solution and CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9a1dcded8334ec3a1bb04fdd71ea35f
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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