Cesium carbonate → 5-Cyclopropylpyridin-3-amine

HRID 2171242Notes

Reaction equation

[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1.O.Br[C:21]1[CH:22]=[C:23]([NH2:27])[CH:24]=[N:25][CH:26]=1>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.O>[CH:1]1([C:21]2[CH:22]=[C:23]([NH2:27])[CH:24]=[N:25][CH:26]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

Cyclopropylboronic acid (360 mg), cesium carbonate (1.4 g), and Pd(PPh3)4 (166 mg) were added to a 1,4-dioxane/water (4.5 ml/0.5 ml) solution containing 5-bromopyridin-3-amine (500 mg) in a nitrogen atmosphere, followed by stirring in a sealed tube at 100° C. for 5 hours. The reaction solution was adjusted to room temperature and water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 30:1). A brown solid of 5-cyclopropyl pyridin-3-amine (314 mg) was thus obtained.

Workup

customwas adjusted to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layers were washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled away under reduced pressure
customthe obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 30:1)

Sources & evidence

ORD record: ord-794a78d0be494970a4d12b919ed4c965
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051310B2

Reaction notes

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