Cesium carbonate → Tert-butyl (2-[(5-bromopyridin-3-yl)amino]ethyl)carbamate

HRID 2307818Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[NH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>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]>[C:15]([O:14][C:13](=[O:19])[NH:12][CH2:11][CH2:10][NH:9][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A 50 mL RBF was charged with 3,5-dibromopyridine (3.70 g, 15.6 mmol), t-butyl N-(2-aminoethyl)carbamate (2.50 g, 15.6 mmol), Pd2(dba)3 (714 mg, 0.78 mmol), (R)-BINAP (1.46 g, 2.34 mol) and Cs2CO3 (7.62 g, 23.4 mmol), and was purged with N2. Anhydrous toluene (120 mL) was added via syringe. The solution was purged with N2 again, and was heated at 100° C. overnight. After cooled, ethyl acetate (500 mL) was added and the mixture was washed with water. The EtOAc solution was concentrated and the residue was separated by flash chromatography (20-80% EtOAc in hexane) to provide the desried product (2.1 g, 43%). MS (DCI) m/z 316, 318 (M+1)+.

Workup

customwas purged with N2
additionAnhydrous toluene (120 mL) was added via syringe
customThe solution was purged with N2 again
temperatureAfter cooled
additionethyl acetate (500 mL) was added
washthe mixture was washed with water
concentrationThe EtOAc solution was concentrated
customthe residue was separated by flash chromatography (20-80% EtOAc in hexane)

Sources & evidence

ORD record: ord-c27eca477e5647fdae44744f80cfe1ca
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831175B2

Reaction notes

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