Potassium Carbonate → HCID 15341802, compound

HRID 1033628Notes

Reaction equation

HRID 1033628 reaction equation
[CH:1]1([CH2:4][C:5]2[C:6]([OH:16])=[C:7]([CH:12]=[CH:13][C:14]=2[OH:15])[C:8]([NH:10][CH3:11])=[O:9])[CH2:3][CH2:2]1.I[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:35]=[CH:34][C:25]2[CH2:26][CH2:27][CH:28]([C:30]([O:32][CH3:33])=[O:31])[O:29][C:24]=2[C:23]=1[CH2:36][CH:37]=[CH2:38].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]1([CH2:4][C:5]2[C:6]([OH:16])=[C:7]([C:8]([NH:10][CH3:11])=[O:9])[CH:12]=[CH:13][C:14]=2[O:15][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:35]=[CH:34][C:25]3[CH2:26][CH2:27][CH:28]([C:30]([O:32][CH3:33])=[O:31])[O:29][C:24]=3[C:23]=2[CH2:36][CH2:37][CH3:38])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 153418003-(Cyclopropylmethyl)-2,4-dihydroxy-N-methylbenzamideHCID 15341801HCID 15341801, compound

Product 1

HCID 15341802HCID 15341802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 16 (50 mg, 0.226 mmol), methyl 3,4-dihydro-7-(3-iodopropoxy)-8-(2-propenyl)-2H-1-benzopyran-2-carboxylate (95 mg, 0.226 mmol), and potassium carbonate (78 mg, 0.565 mmol) were added to 10 ml of DMF, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water and extracted with ethyl acetate then dried over magnesium sulfate and concentrated in vacuo to give the crude product. Chromatography of the crude product on silica gel using 15% ethyl acetate/85% hexane as eluant provided the product.

Workup

  1. washThe reaction mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialthen dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude product

Sources & evidence

ORD record
ord-4753e5d840944cbdba265c6f1ed2735b
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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