Methyl 2-isocyanatobenzoate → HCID 58677535, compound

HRID 1012627Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])=[O:9])[CH:7]=1.[N:27]([C:30]1[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=1[C:32]([O:34][CH3:35])=[O:33])=[C:28]=[O:29]>O1CCOCC1>[CH3:35][O:34][C:32](=[O:33])[C:31]1[CH:36]=[CH:37][CH:38]=[CH:39][C:30]=1[NH:27][C:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])[CH:7]=1)=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 494 (0.03 g, 0.08 mmol) was dissolved in 1,4-dioxan (0.5 mL) and methyl 2-isocyanatobenzoate (0.021 mL, 0.12 mmol) was added. The solution was stirred at 50° C. for 24 h. Methyl 2-isocyanatobenzoate (0.01 mL, 0.06 mmol) was added. The solution was stirred at 50° C. for 24 h. Work up as described in the preparation of compound 259. The crude product was purified by flash chromatography using a gradient of EtOAc/petroleum ether (40-60) 10:90→40:60 as the eluent. This afforded the title compound as yellow oil. 13C NMR (CDCl3) δ 195.8, 169.0, 159.0 (dd), 155.4 (dd), 152.4, 147.6, 142.5, 139.5, 135.6, 135.1, 134.6, 133.6, 133.4, 132.1, 130.8, 129.4, 124.5 (dd), 124.1 (dd), 123.3, 121.7, 121.3, 119.8, 116.3, 114.3, 112.8, 111.5 (dd), 104.9 (dd), 52.2, 19.8

Workup

stirringThe solution was stirred at 50° C. for 24 h
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-46a60ef369bb4633a1fa4298d03a9cf2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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