Trifluoroacetic acid → 5-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

HRID 448561Notes

Reaction equation

HRID 448561 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([N:21]3[C:29]4[C:24](=[CH:25][C:26]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:27][CH:28]=4)[CH2:23][CH2:22]3)[N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:33][S:30]([C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[N:21]([C:19]1[CH:20]=[C:15]([O:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:16]=[CH:17][N:18]=1)[CH2:22][CH2:23]2)(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25242414Tert-butyl 4-((6-(5-(methylsulfonyl)indolin-1-yl)pyrimidin-4-yl)oxy)piperidine-1-carboxylate

Product 1

HCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indolineYield 131.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4a (0.55 g) in 8 mL of DCM, was added trifluoroacetic acid (3 mL, 33 eq) at room temperature. The reaction mixture was stirred at room temperature for 3 h then the solvent and excess trifluoroacetic acid were removed under a stream of nitrogen to give 0.57 g of 4b.

Workup

  1. customthe solvent and excess trifluoroacetic acid were removed under a stream of nitrogen

Sources & evidence

ORD record
ord-975deb1ff1774b5c9579b32a0e7ff18b
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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