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

HRID 511511Notes

Reaction equation

Br[CH2:2][C:3]1[N:8]=[CH:7][C:6]([N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1.[P:24]([O:31]CC)([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27]>C1(C)C(C)=CC=CC=1>[C:13]([O:12][C:10]([N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])=[N:8][CH:7]=1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

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, 6 H), 1.39 (s, 18 H), 3.43 (d, J=22.0 Hz 2 H), 4.09-4.18 (m, 4 H), 7.43 (dd, J=2.0, 8.0 Hz, 1 H), 7.67 (s, 1 H), 8.33 (d, J=8.0 Hz, 1 H).

Workup

concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-10e0f57b807a4c009375c2ee13887ced
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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