Iodoethane → Methyl 1-[ethyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylate

HRID 1479844Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:26][CH3:27]>CN(C=O)C>[CH2:26]([N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[C:12]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13]1)[CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 13A (1 g, 3.67 mmol) in DMF (15 mL) was added with an. K2CO3 (1.5 mol eq, 0.76 g) and, after few minutes, 2-iodoethane (1.2 mol eq, 0.45 ml) was added and the mixture was heated at 50° C. for 12 h. The solvent was removed under reduced pressure, water was added to the residue (60 mL) and the aqueous phase was extracted with EtOAc (3×30 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 14A as a pale yellow oil (1.1 g, 98% yield). 1HNMR (DMSO, 200 MHz) δ 1.095 (t, 3H, J=8), 4.43 (bs, 4H), 2.88 (s, 3H), 3.32 (m, 2H), 7.42 (t, 2H, J=8.2), 7.87 (m, 2H).

Workup

customThe solvent was removed under reduced pressure, water
additionwas added to the residue (60 mL)
extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-c452593aa1884ca0936fb30df7cf7dc1
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

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