Potassium Carbonate → 4-Cyclopent-1-en-1-ylpyridine-2-amine

HRID 337770Notes

Reaction equation

HRID 337770 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)[CH2:13][CH2:12][CH2:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C>[C:9]1([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)[CH2:13][CH2:12][CH2:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5818662-Amino-4-chloropyridineHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 899623244-Cyclopent-1-en-1-ylpyridine-2-amineYield 41.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 33a by using the 2-amino-4-chloropyridine (1.07 g, 8.32 mmol), 2-cyclopent-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.61 g, 8.29 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(303 mg, 0.414 mmol), potassium carbonate (4.59 g, 33.2 mmol) and DMF (15 mL), to yield the title compound (552 mg, 41%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-4259f2e046d24e9cb17bc3f40e731bcd
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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