Water → Methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

HRID 516052Notes

Reaction equation

HRID 516052 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:14]([N:16]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[N:17]1)[CH3:15].C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.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.CCOC(C)=O>[C:12]([C:8]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([C:19]2[CH:18]=[N:17][N:16]([CH2:14][CH3:15])[CH:20]=2)[N:11]=[CH:10][CH:9]=1)#[N:13]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 58317566Methyl 2-chloro-4-cyanonicotinate

Product 1

HCID 58317527Methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinateYield 114.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-chloro-4-cyanonicotinate (207 mg, 1.053 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (201 mg, 0.905 mmol) and tetrakis(triphenylphosphine)palladium(0) (122 mg, 0.105 mmol) in DME (2 mL), and saturated aq Na2CO3 (2 mL) was stirred at 80° C. for 3 h under N2 atmosphere. Water and EtOAc were subsequently added. The organic phase was washed with H2O and brine, dried over MgSO4, and evaporated to yield the title compound (265.3 mg, 98%). [M+H] calc'd for C13H12N4O2, 257; found, 257.

Workup

  1. washThe organic phase was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-a0befa56f5224bb888a2ef6dbeb91f95
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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