Potassium Carbonate → 4-Cyclohex-1-en-1-ylpyridin-2-amine

HRID 337768Notes

Reaction equation

HRID 337768 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]1(B2OC(C)(C)C(C)(C)O2)[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>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>[C:9]1([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5818662-Amino-4-chloropyridineHCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 899633784-Cyclohex-1-en-1-ylpyridin-2-amineYield 14.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 33a by using 2-amino-4-chloropyridine (927 mg, 7.21 mmol), 2-cyclohex-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.50 g, 7.21 mmol), tetrakis(triphenylphosphine)palladium (0) (416 mg, 0.360 mmol), potassium carbonate (3.98 g, 14.5 mmol) and DMF (13 mL), to yield the title compound (180 mg, 14%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-3ac549bd32b64c5bada77f48b3aa5ae4
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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