Cesium carbonate → Tert-butyl 2-(2,6-dimethylpyridin-4-ylamino)propylcarbamate

HRID 333081Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.Cl.[NH2:11][CH:12]([CH3:22])[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:8][C:6]1[CH:7]=[C:2]([NH:11][CH:12]([CH3:22])[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:3]=[C:4]([CH3:9])[N:5]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-Chloro-2,6-dimethylpyridine (131 mg, 0.925 mmol), tert-butyl 2-aminopropylcarbamate hydrochloride (151 mg, 0.717 mmol), cesium carbonate (750 mg, 2.302 mmol), and anhydrous 1,4-dioxane (3 ml) was treated with tris(dibenzylideneacetone)dipalladium(0) (39 mg, 0.043 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (74 mg, 0.128 mmol) under an atmosphere of argon. The mixture was heated at 110° C. for 8 hours, allowed to reach room temperature and filtered. The filter residue was washed with DCM, the combined filtrates were evaporated. The residue was purified by column chromatography using a gradient of methanol (1-10%) in dichloromethane to yield 241 mg of a yellow oil. MS (ESI) m/z=280.2.

Workup

customto reach room temperature
filtrationfiltered
washThe filter residue was washed with DCM
customthe combined filtrates were evaporated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-a7423fa2f09649a0b3c6b5e3c80a81ad
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877934B2

Reaction notes

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