Methyl iodide → Ethyl 9-bromo-4-(methoxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

HRID 575295Notes

Reaction equation

HRID 575295 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][CH2:7][CH:8]([CH2:19][OH:20])[C:9]3[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.[CH3:23]I>ClCCl.[Ag]=O>[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][CH2:7][CH:8]([CH2:19][O:20][CH3:23])[C:9]3[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 86693325Ethyl 9-bromo-4-(hydroxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

Product 1

HCID 86693326Ethyl 9-bromo-4-(methoxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylateYield 53.1%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 9-bromo-4-(hydroxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (200 mg, 0.52 mmol, 1.00 equiv), MeI (750 mg, 5.28 mmol, 10.00 equiv) and silver oxide (480 mg, 2.07 mmol, 4.00 equiv) in dichloromethane (15 mL) was stirred for 6 h at 50° C. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:10) to give 110 mg (53%) of the titled compound as an off-white solid; LC-MS (ES, m/z) 398,400 [M+H]+.

Workup

  1. filtrationThe solids were filtered out
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:10)

Sources & evidence

ORD record
ord-7bd8e4a22d264f6d8be157b5e4035723
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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