Pyridine, hydrofluoride (1:1) → Ethyl 9-bromo-4-fluoro-4-(hydroxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

HRID 575296Notes

Reaction equation

HRID 575296 reaction equation
C1C=CN=CC=1.[FH:7].[Br:8][C:9]1[CH:29]=[CH:28][C:12]2[O:13][CH2:14][C:15]3([C:18]4[S:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:20][C:19]=4[C:11]=2[CH:10]=1)[CH2:17][O:16]3>ClCCl>[Br:8][C:9]1[CH:29]=[CH:28][C:12]2[O:13][CH2:14][C:15]([F:7])([CH2:17][OH:16])[C:18]3[S:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:20][C:19]=3[C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 86693323HCID 86693323, compound

Product 1

HCID 89754666Ethyl 9-bromo-4-fluoro-4-(hydroxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

HF-pyridine (70%) (2 mL) was added dropwise to a stirred solution of ethyl 9-bromo-5H-spiro[benzo[2,3]oxepino[4,5-d]thiazole-4,2′-oxirane]-2-carboxylate (600 mg, 1.57 mmol, 1.00 equiv) in dichloromethane (10 mL) at 0° C. After being stirred for 1 h at 0° C. the reaction was quenched with brine, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:10) to give 270 mg (43%) of the titled compound as a off-white solid; LC-MS (ES, m/z) 402, 404 [M+H]+.

Workup

  1. customwas quenched with brine
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:10)

Sources & evidence

ORD record
ord-45379acd6f374568a6ba7dd6ad5f0626
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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