Sodium Iodide → HCID 58677566, compound

HRID 1012647Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:18]=3[CH3:24])=[O:16])=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=2)=[C:4]([CH3:28])[CH:3]=1.Cl.Cl[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[C:21]([O:23][CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:20]=[CH:19][C:18]=3[CH3:24])=[O:16])=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=2)=[C:4]([CH3:28])[CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Compound 505 (0.083 g, 0.22 mmol) and N-(2-chloroethyl)morpholine hydrochloride (0.082 g, 0.44 mmol) were suspended in CH3CN (5 mL). K2CO3 (0.17 g, 1.2 mmol) and NaI (0.008 g, 0.05 mmol) were added and the suspension was heated in a microwave oven at 130° C. for 40 minutes. The suspension was filtered and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography using a gradient of EtOAc/petroleum ether (40-60) 2:3→1:0 as the eluent. This afforded the title compound. 1H NMR (CDCl3) δ 7.34 (d, 1H), 7.21 (dd, 1H), 7.17 (d, 1H), 7.10 (d, 1H), 7.05-6.88 (m, 3H), 6.85-6.78 (m, 2H), 6.16 (s, 1H), 4.02 (t, 2H), 3.72 (m, 4H), 2.75 (t, 2H), 2.54 (m, 4H), 2.45 (s, 3H), 2.25 (s, 3H)

Workup

filtrationThe suspension was filtered
concentrationthe filtrate was concentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-a3e3a0acac974d9cadc3800d558c5398
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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