Potassium Carbonate → HCID 23433059, compound

HRID 2121359Notes

Reaction equation

HRID 2121359 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH2:15]([N:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][NH2:21])[CH3:16].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C(N(CC)CC)C.C1(C)C=CC=CC=1.O1CCCC1.CO>[CH2:15]([N:17]([CH2:18][CH2:19][CH2:20][NH:21][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:22][CH3:23])[CH3:16]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 61011N,N-Diethyl-1,3-propanediamineHCID 2762480tert-Butyl 2-chloropyridine-4-carboxylate

Product 1

HCID 23433059HCID 23433059, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 67132910HCID 67132910, compoundSolvent

Procedure

1.02 g (4.77 mmol) of tert-butyl 2-chloroisonicotinate, 5 ml of 3-diethylamino-1-propylamine, 0.66 g (4.77 mmol) of potassium carbonate, a spatula tip of Cu powder and a spatula tip of 18-crown-6 were refluxed for 4 hours. Flash chromatography of the reaction mixture (toluene/tetrahydro-furan/methanol, 4/1/1+2.5% triethylamine) resulted in 0.69 g of pale brown oil.

Sources & evidence

ORD record
ord-023225fe5f9d45259b1ec278f328c147
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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