Trifluoroacetic acid → (R)-5-(4-(piperidin-3-yl)-1H-1,2,3-triazol-1-yl)-3-(pyridin-4-yl)-1H-indazole

HRID 1465687Notes

Reaction equation

HRID 1465687 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[CH:20]=[C:19]([C@@H:21]5[CH2:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]5)[N:18]=[N:17]4)[CH:14]=3)[N:9](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:8]=2)=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[NH:23]1[CH2:24][CH2:25][CH2:26][C@@H:21]([C:19]2[N:18]=[N:17][N:16]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[NH:9][N:8]=[C:7]4[C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH:20]=2)[CH2:22]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67517916(R)-tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl)piperidine-1-carboxylate

Product 1

HCID 86695572(R)-5-(4-(piperidin-3-yl)-1H-1,2,3-triazol-1-yl)-3-(pyridin-4-yl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the crude (R)-tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl)piperidine-1-carboxylate dissolved in CH2Cl2 (30 mL) was added TFA (2 mL and Et3SiH (0.2 mL) and stirred at room temperature overnight under a stream of nitrogen. Evaporated the solvent and column purified (10% MeOH in CH2Cl2) to give the (R)-5-(4-(piperidin-3-yl)-1H-1,2,3-triazol-1-yl)-3-(pyridin-4-yl)-1H-indazole (0.61 g).

Workup

  1. customEvaporated the solvent and column
  2. custompurified (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4175344f5fde4430839d767fcb1cb465
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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