Diiodomethane → HCID 68628672, compound

HRID 572614Notes

Reaction equation

N[C:2]1[C:6]([C:7]#[N:8])=[C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:4][C:3]=1[C:15]([O:17][CH3:18])=[O:16].[I:19]CI.N(OCCCCC)=O>C(#N)C>[C:7]([C:6]1[C:2]([I:19])=[C:3]([C:15]([O:17][CH3:18])=[O:16])[S:4][C:5]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)#[N:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-amino-4-cyano-5-morpholin-4-ylthiophene-2-carboxylate (3.4 g, 12.6 mmol) in ACN (110 mL) was added diiodomethane (10.5 mL, 130.2 mmol) and amyl nitrite (1.1 mL, 77.7 mmol). The reaction mixture was allowed to stir at 80° C. for 4 days and was concentrated. The residue was purified by column chromatography to give methyl 4-cyano-3-iodo-5-morpholin-4-ylthiophene-2-carboxylate (2.2 g, 46%). LCMS: (FA) ES+ 379.0. 1H NMR (400 MHz, d6-DMSO) δ: 3.76 (s, 3H), 3.72-3.75 (m, 4H) and 3.56-3.61 (m, 4H).

Workup

concentrationwas concentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-70755cbba2ea4d52bc10d12a409cee73
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029411B2

Reaction notes

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