Tetrahydrofuran → HCID 58504183, compound

HRID 2407700Notes

Reaction equation

HRID 2407700 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:5]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:23]1([C:29]2[CH:33]=[C:32]([CH2:34][N:35]3[CH2:40][CH2:39][CH:38]([CH2:41][NH2:42])[CH2:37][CH2:36]3)[O:31][N:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C.O1CCCC1>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:42]([CH2:41][CH:38]1[CH2:37][CH2:36][N:35]([CH2:34][C:32]3[O:31][N:30]=[C:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:33]=3)[CH2:40][CH2:39]1)[C:6]([OH:7])([C:13]([O:15][CH3:16])=[O:14])[CH:5]2[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 58504252HCID 58504252, compoundHCID 66990710Methyl 6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylate

Product 1

HCID 58504183HCID 58504183, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylate (0.319 g, prepared according to the reported preparation in US 2005/0148624) and the compound prepared in Example 9 (0.458 g) were suspended in methanol (10 mL) and diisopropylethylamine (0.772 mL) was added. Tetrahydrofuran (5 mL) was added and the reaction mixture was heated at 60° C. overnight. The reaction mixture was then cooled to room temperature and concentrated. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organics were washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate) to obtain the title compound (0.560 g) having the following physical data.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated
  3. customThe reaction mixture was partitioned between ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-6aa578f87fc245cfafb450d1169387d9
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…