Cesium carbonate → HCID 86723802, compound

HRID 577576Notes

Reaction equation

HRID 577576 reaction equation
[Br:1][C:2]1[C:3]([CH3:24])=[C:4]([C:20](F)=[CH:21][CH:22]=1)[C:5]([N:7]([CH2:17][CH2:18][OH:19])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:6].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:22]=[CH:21][C:20]2[O:19][CH2:18][CH2:17][N:7]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[C:5](=[O:6])[C:4]=2[C:3]=1[CH3:24]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86723801HCID 86723801, compound

Product 1

HCID 86723802HCID 86723802, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-bromo-6-fluoro-N-(2-hydroxyethyl)-N-(4-methoxybenzyl)-2-methylbenzamide (130b, 5.00 g, 12.6 mmol) and Cs2CO3 (8.20 g, 25.3 mmol) in dry DMF (60 mL) was stirred at 65° C. for 14 hours. To the reaction mixture was added brine (100 mL). The mixture was extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (4×60 mL), dried over Na2SO4, and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 5/1) to give 7-bromo-4-(4-methoxybenzyl)-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (130c, 2.8 g, 59%) as a colorless oil.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×50 mL)
  2. washThe combined organic layers were washed with brine (4×60 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography (petroleum ether/EtOAc, 5/1)

Sources & evidence

ORD record
ord-19b4ef1d2f554702b0444904fe6c5f4e
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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