Dimethylformamide → HCID 18771018, compound

HRID 1786821Notes

Reaction equation

HRID 1786821 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]2([CH:22]=[C:21]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([OH:30])=[C:25]([F:31])[CH:24]=3)[C:20]3[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=3[O:18]2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C.O>[CH2:5]([N:12]1[CH2:13][CH2:14][C:15]2([CH:22]=[C:21]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([O:30][CH2:3][CH:2]=[CH2:1])=[C:25]([F:31])[CH:24]=3)[C:20]3[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=3[O:18]2)[CH2:16][CH2:17]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 18770969HCID 18770969, compound

Product 1

HCID 18771018HCID 18771018, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl bromide (1.1 mole equiv.) was added dropwise to a mixture of N-benzyl-4-(3,5-difluoro-4-hydroxyphenyl)spiro[2H-1-benzopyran-2,4′-piperidine](750 mg, 1.79 mmol; prepared according to the procedures outlined in Examples 1 and 42), cesium carbonate (1.1 mole equiv.) and anhydrous N,N-dimethylformamide (15 cm3). After stirring for 2 h at room temperature no starting material remained. The reaction mixture was diluted with ethyl acetate (50 cm3) and treated with water (100 cm3) the aqueous layer was separated and re-extracted with ethyl acetate (2×25 cm3). The combined organic extracts were washed with water (4×100 cm3) before being dried (Na2SO4) and the volatile materials were removed in vacuo to afford the desired material in high purity (60%).

Workup

  1. customprepared
  2. customwas separated
  3. extractionre-extracted with ethyl acetate (2×25 cm3)
  4. washThe combined organic extracts were washed with water (4×100 cm3)
  5. dry with materialbefore being dried (Na2SO4)
  6. customthe volatile materials were removed in vacuo

Sources & evidence

ORD record
ord-a9e982245fb241d4b5681fd7f58c0ba0
Source dataset
uspto-grants-2009_03
Patent number
US07507824B2

Reaction notes

Loading…