Dichloromethane → HCID 59432333, compound

HRID 507088Notes

Reaction equation

HRID 507088 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].CB(O)O.ClCCl.[CH:14]([O:17][C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[C:22]2[CH:28]=[CH:29][C:30](Br)=[C:31]([CH3:32])[C:21]1=2)=[O:19])([CH3:16])[CH3:15]>O1CCOCC1>[CH:14]([O:17][C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[C:22]2[CH:28]=[CH:29][C:30]([CH3:1])=[C:31]([CH3:32])[C:21]1=2)=[O:19])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 139377Methylboronic AcidHCID 59432457HCID 59432457, compound

Product 1

HCID 59432333HCID 59432333, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Add cesium carbonate (456 mg, 3.0 mmol), methyl boronic acid (90 mg, 1.5 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (82 mg, 0.1 mmol) to a solution of 8-bromo-9-methyl-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (341 mg, 1.0 mmol) in dioxane (8 mL). Stir the mixture under nitrogen at 110° C. for 1 h and 30 min. Cool down the mixture to room temperature and filter over Celite® washing with ethyl acetate. Evaporate the solvent and purify the crude by chromatography, eluting with hexane/ethyl acetate to afford the title compound (239 mg, 87%). MS (ES+): 276 (M+H).

Workup

  1. custom30 min
  2. temperatureCool down the mixture to room temperature
  3. filtrationfilter over Celite®
  4. washwashing with ethyl acetate
  5. customEvaporate the solvent
  6. custompurify the crude by chromatography
  7. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-e7a3791320954334a6dfb8c1a590f790
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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