Dimethylformamide → HCID 57683735, compound

HRID 495145Notes

Reaction equation

HRID 495145 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].[C:14]([O-:17])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+].CN([CH:29]=[O:30])C>CC(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][C:7](=[O:12])[CH:6]=[C:5]([O:13][CH2:11][CH2:2][CH2:3][O:17][CH:14]3[CH2:9][CH2:4][CH2:5][CH2:29][O:30]3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 546914046-Bromo-4-hydroxy-2H-1-benzopyran-2-one

Product 1

HCID 57683735HCID 57683735, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

6-Bromo-4-hydroxycoumarin (1.19 mmol, 0.287 g), K2CO3 (3.57 mmol, 0.493 g) and 2-3-(bromopropoxy)tetrahydro-2H-pyran (1.19 mmol, 0.264 g) is suspended in 10 mL of acetone, and is heated to 55° C. for 24 hrs at which time the reaction is not complete. Cs2CO3 (1.54 mmol, 0.5 g) and 5 mL of DMF are added and the reaction is heated for an additional 2 hrs. Twenty-five percent of the crude THP protected material is purified by HPLC to afford the title compound (70.8 mg, 62%); 1H NMR (CDCl3, 300 MHz) δ 7.91 (1H, d, J=2.25 Hz), 7.82 (1H, dd, J=2.5, 9 Hz), 7.39 (1H, d, J=9 Hz), 5.98 (1H, s), 4.59 (1H, m), 4.31 (2H, t, J=6 Hz), 3.83 (1H, m), 3.72 (1H, m), 3.55 (2H, m), 2.09 (2H, m), 1.65 (2H, m), 1.45 (4H, m); MS (ESI, Pos.) calcd for C17H19BrO5 m/z [M+H]=383.0, found 383.1.

Workup

  1. temperaturethe reaction is heated for an additional 2 hrs
  2. customTwenty-five percent of the crude THP protected material is purified by HPLC

Sources & evidence

ORD record
ord-77b88439654e43369396ba1c3aa50b82
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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