Boron trifluoride → Ethyl 9-bromo-4-(hydroxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

HRID 575294Notes

Reaction equation

HRID 575294 reaction equation
B(F)(F)F.[Br:5][C:6]1[CH:26]=[CH:25][C:9]2[O:10][CH2:11][C:12]3([C:15]4[S:19][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:17][C:16]=4[C:8]=2[CH:7]=1)[CH2:14][O:13]3.[SiH](CC)(CC)CC>ClCCl.C([O-])(O)=O.[Na+]>[Br:5][C:6]1[CH:26]=[CH:25][C:9]2[O:10][CH2:11][CH:12]([CH2:14][OH:13])[C:15]3[S:19][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:17][C:16]=3[C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 86693323HCID 86693323, compound

Product 1

HCID 86693325Ethyl 9-bromo-4-(hydroxymethyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Boron trifluoride diethleherate (0.16 mL, 1.00 equiv) 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 (500 mg, 1.31 mmol, 1.00 equiv) and Et3SiH (227.5 mg, 1.96 mmol, 1.50 equiv) in dichloromethane (25 mL) at 0° C. After being stirred for 15 min at room temperature the reaction solution was diluted with 50 mL of aqueous NaHCO3, 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 (1:3) to give 340 mg (68%) of the titled compound as a off-white solid; LC-MS (ES, m/z) 384,386 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-599495e1caa74ad3a2a1bd7f48c36d73
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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