4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester → 1-(5-chlorothiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine

HRID 1437178Notes

Reaction equation

HRID 1437178 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]3[S:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[Cl:29][C:26]1[S:25][C:24]([CH2:23][N:16]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:15]2)=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 688942864-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 179729751-(5-chlorothiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridineYield 127.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Over a solution of 2.86 g (6.6 mmol) of 4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester in 20 ml of dichloromethane, 5.1 ml of trifluoroacetic acid were added. After 1 hour at room temperature, the solvent was removed under reduced pressure. The crude mixture was dissolved in ethyl acetate and washed with saturated solution of potassium carbonate and brine. The organic phase was dried over magnesium sulphate, filtered and removed under reduced pressure affording 2.8 g of a crude mixture which was pure enough for the next synthetic step.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe crude mixture was dissolved in ethyl acetate
  3. washwashed with saturated solution of potassium carbonate and brine
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-cc94ff028c0c463e8785f153e81140ef
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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