Water → HCID 59277611, compound

HRID 1362422Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:13])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br.[Br:21][C:22]1[CH:23]=[C:24]([CH2:29]Br)[C:25]([NH2:28])=[N:26][CH:27]=1.O>CN(C=O)C>[NH2:28][C:25]1[C:24]([CH2:29][N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:23][C:22]([Br:21])=[CH:27][N:26]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of phenyl glycine ethyl ester (4.94 g, 27.6 mmol) and K2CO3 (11.42 g, 82.7 mmol) in anhydrous DMF (300 mL) under argon was added 5-bromo-3-(bromomethyl)pyridin-2-amine hydrobromide (9.52 g, 27.6 mmol). The mixture was stirred for 12 h at 40° C. Water (500 mL) was added and the mixture was extracted with ethyl acetate (3×500 mL). Combined organic layers were washed with water (2×400 mL) and brine (400 mL), dried over MgSO4, filtered and concentrated to a brown oil. Purification by column chromatography (silica gel, gradient elution of 30% ethyl acetate/hexanes to 80% ethyl acetate/hexanes) gave ethyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(phenyl)amino)acetate (3.41 g, 34%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 7.89-7.88 (m, 1H), 7.36-7.35 (m, 1H), 7.17-7.11 (m, 2H), 6.68-6.64 (m, 1H), 6.47-6.44 (m, 2H), 6.09 (s, 2H), 4.30-4.29 (m, 4H), 4.12 (q, J=6.9 Hz, 2H), 1.19 (t, J=6.9 Hz, 3H).

Workup

extractionthe mixture was extracted with ethyl acetate (3×500 mL)
washCombined organic layers were washed with water (2×400 mL) and brine (400 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to a brown oil
customPurification
washby column chromatography (silica gel, gradient elution of 30% ethyl acetate/hexanes to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-42dfbc4e840a498c8cc26de1fb5c5e9d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879872B2

Reaction notes

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