Triethyl phosphite → Diethyl ({5-[bis(tert-butoxycarbonyl)amino]pyridin-2-yl}methyl)phosphonate

HRID 1948079Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:16]1[CH:17]=[N:18][C:19]([CH2:22]Br)=[CH:20][CH:21]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[P:24]([O:31]CC)([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27]>C1(C)C(C)=CC=CC=1>[CH2:26]([O:25][P:24]([CH2:22][C:19]1[CH:20]=[CH:21][C:16]([N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:17][N:18]=1)(=[O:31])[O:28][CH2:29][CH3:30])[CH3:27]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of di-tert-butyl[6-(bromomethyl)pyridin-3-yl]imidodicarbonate (Compound 260C, 3.0 g, 7.7 mmol) in dry xylene (100 mL) was added a triethyl phosphite (6.0 g, 36 mmol). The reaction mixture was stirred at 140° C. for 4 h, then concentrated. The residue was purified by column chromatography to give the desired compound (2.5 g, yield: 92%) as a liquid. 1H NMR (CDCl3, 400 MHz): δ=1.34 (t, J=7.6 Hz, 6H), 1.39 (s, 18H), 3.43 (d, J=22.0 Hz 2H), 4.09-4.18 (m, 4H), 7.43 (dd, J=2.0, 8.0 Hz, 1H), 7.67 (s, 1H), 8.33 (d, J=8.0 Hz, 1H).

Workup

concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-afad7f06636a4191b05e25bc1b8a2b58
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399433B2

Reaction notes

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