Triethylamine → 2-(6-Isocyano-2,7-naphthyridin-1-yl)isoindoline-1,3-dione

HRID 874694Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[N:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[CH:20]=[N:19][C:18]([NH:22][CH:23]=O)=[CH:17]2.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl>[N+:22]([C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][N:19]=1)[C:12]([N:3]1[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]1=[O:11])=[N:13][CH:14]=[CH:15]2)#[C-:23]

Participants

Conditions

Temperature: 0 °C

Procedure

4-8 (90.0 mg, 0.280 mmol) was suspended in CH2Cl2 (10 mL) and cooled to 0° C. To the mixture were added triphosgene (252 mg, 0.85 mmol) followed by Et3N (0.240 mL, 1.69 mmol). The mixture was stirred at room temperature for 2 h. The mixture was diluted with CH2Cl2, washed with saturated aqueous NaHCO3, brine, and dried over Na2SO4. The residue was purified by silica gel chromatography (0-5% EtOAc in CH2Cl2) to give 73.3 mg (41%) of 4-9 as a pale white solid: 1H NMR (300 MHz, CDCl3) δ 9.18 (1H, br s), 8.86 (1H, d, J=5.7 Hz), 8.06 (2H, m), 7.90 (2H, m), 7.85 (1H, br s), 7.84 (1H, d, J=5.7 Hz); ESI-MS m/z 301 [C17H8N4O2+H]+.

Workup

washwashed with saturated aqueous NaHCO3, brine
dry with materialdried over Na2SO4
customThe residue was purified by silica gel chromatography (0-5% EtOAc in CH2Cl2)

Sources & evidence

ORD record: ord-9f74fb8e5a9e46fd8458cf27aad0f2ce
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980916B2

Reaction notes

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