Cesium carbonate → tert-butyl 4-(3-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

HRID 1775027Notes

Reaction equation

HRID 1775027 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[N:8]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[N:7]=2)=[N:2]1.[C:27]([N:34]1[CH2:39][CH2:38][CH:37](Br)[CH2:36][CH2:35]1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:12]2[CH:13]=[C:14]3[C:6]([C:3]4[CH:4]=[CH:5][N:1]([CH:37]5[CH2:38][CH2:39][N:34]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:35][CH2:36]5)[N:2]=4)=[N:7][N:8]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:9]3=[CH:10][N:11]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 15541517tert-Butyl 4-bromopiperidine-1-carboxylateHCID 178420767HCID 178420767, compound

Product 1

HCID 71253610tert-butyl 4-(3-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (44.0 mg, 0.13 mmol), 1-N—BOC-4-bromopiperidine (100.8 mg, 0.38 mmol), and Cesium Carbonate (124.3 mg, 0.38 mmol) in N,N-Dimethylformamide (5 mL) was heated at 100° C. for 7 days. The mixture was concentrated to afford tert-butyl 4-(3-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate, which was used without purification.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-68b3f2aeebee4a0c8077d20ea7df08d4
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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