Triethyl phosphite → HCID 17834913, compound

HRID 1879562Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:11]([N+:22]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(OCC)(OCC)OCC>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=3[NH:22]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 66934266HCID 66934266, compound

Product 1

HCID 17834913HCID 17834913, compoundYield 50%

Conditions

Temperature: 160 °C

Procedure

To a pressure resistant vial, was added Compound 7 (2.00 g, 6.22 mmol and Triethyl phosphite (6.53 ml, 37.3 mmol. The mixture was heated to 160° C. overnight. The reaction mixture was concentrated in vacuo. The residue was suspended in chloroform (20 mL), solid precipitate formed and was filtered and washed with ether (10 mL×2) to afford Compound 8 (900 mg, 3.11 mmol, 50.0% yield). 1H-NMR (400 MHz, DMSO) δ: 10.81 (br, 1H), 9.25 (br, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.72 (d, J=8.4 Hz, 1H), 7.50-7.33 (m, 5H), 6.95 (s, 1H), 6-78-6.76 (m, 2H), 6.56 (dd, J=8.4, 2.0 Hz 1H), 5.16 (s, 2H); LRMS for C19H15NO2+H+, calc'd: 290.1. found: 290.1 (M+H+).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customsolid precipitate formed
filtrationwas filtered
washwashed with ether (10 mL×2)

Sources & evidence

ORD record: ord-c49a1d6b209b4949a0f041aef267f1e2
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318132B2

Reaction notes

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