1,4-Dioxane → Ethyl 1'-amino-6'-bromo-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate

HRID 1503449Notes

Reaction equation

HRID 1503449 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:27][CH2:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23]3)[C:8]2([NH:16]S(C(C)(C)C)=O)[C:11]([O:13][CH2:14][CH3:15])=C)=[CH:4][CH:3]=1.[O:30]1CCOCC1>>[NH2:16][C:8]1([C:11]([O:13][CH2:14][CH3:15])=[O:30])[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[CH2:6][C:7]21[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[CH2:26][CH2:27]2

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 58198087N-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 58197140Ethyl 1'-amino-6'-bromo-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylateYield 38%

Procedure

To solution of compound 5 (100 mg, 0.26 mmol) and Lawesson'reagent (104 mg, 0.26 mmol) in dioxane (3 mL) was heated at 150° C. for 30 min in a microwave reactor. The mixture was cooled, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexanes:EtOAc=20:1) to give compound 7 (30 mg, 38%) as a light orange solid.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (hexanes:EtOAc=20:1)

Sources & evidence

ORD record
ord-0acea46488974fcab31b6c20da4d908e
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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