Cesium carbonate → HCID 23586864, compound

HRID 489175Notes

Reaction equation

HRID 489175 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][N:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1.[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:8]2[N:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=3)[C:9]2=[O:12])=[CH:23][CH:24]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 178518887HCID 178518887, compound

Product 1

HCID 23586864HCID 23586864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 7-bromo-1-hydroxy-3-azaisoquinoline (7.02 g, 28.2 mmol) in dimethylformamide (75 mL) is treated with 4-bromomethylbenzoic acid tert-butyl ester (12.5 g, 36.7 mmol) and cesium carbonate (11.94 g, 36.7 mmol), then stirred overnight at room temperature. The dimethylformamide is evaporated in vacuo, the residue is diluted with ethyl acetate, washed with 1N HCl, the organic portion washed with brine, dried over MgSO4 and evaporated to dryness. The residue is triturated with hot hexanes/ethyl acetate, cooled to room temperature, and the solid is collected by filtration and dried to give the desired product. Step (2): 4-[1-oxo-7-(3-phenyl-prop-1-ynyl)-1H-3-azaisoquinolin-2-ylmethyl]benzoic acid tert-butyl ester

Workup

  1. customThe dimethylformamide is evaporated in vacuo
  2. additionthe residue is diluted with ethyl acetate
  3. washwashed with 1N HCl
  4. washthe organic portion washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe residue is triturated with hot hexanes/ethyl acetate
  8. temperaturecooled to room temperature
  9. filtrationthe solid is collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-f3425fc5f81b4b7880a56ded3e00e46c
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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