Pyrazole → ethyl 1-(oxan-2-yl)-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazole-3-carboxylate

HRID 60179Notes

Reaction equation

HRID 60179 reaction equation
Br[C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=1.N1C=CC=N1.CC1(C)OB([C:29]2[CH:34]=[CH:33][N:32]=[C:31]3[NH:35][CH:36]=[CH:37][C:30]=23)OC1(C)C.C([O-])(O)=O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[O:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[N:5]1[CH:6]=[C:2]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]3[NH:35][CH:36]=[CH:37][C:30]=23)[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4]1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 516892Sodium BicarbonateHCID 497588714-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 118025309Ethyl 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate

Product 1

HCID 118025456ethyl 1-(oxan-2-yl)-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-bromo-1-(oxan-2-yl)-1H-pyrazole-3-carboxylate (as a mixture of regioisomers of the tetrahydropyran group at the nitrogen atoms of the pyrazole) (7.9 g, 26.23 mmol), 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (6.4 g, 26.23 mmol), and Pd(PPh3)4 (1.8 g, 1.57 mmol) were taken up in a degassed DMF (100 mL) and NaHCO3 (saturated, 50 mL) under an atmosphere of nitrogen.

Sources & evidence

ORD record
ord-cd8d606034574c9aa712c3f0014e252b
Source dataset
uspto-grants-2016_09
Patent number
US09440977B2

Reaction notes

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