Dichloromethane → HCID 78324914, compound

HRID 873532Notes

Reaction equation

HRID 873532 reaction equation
[C:1]([C:3]1[C:4]([C:38]([OH:40])=[O:39])=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]3[C:30]4[C:29](=[O:31])[CH2:28][C:27]([CH3:33])([CH3:32])[CH2:26][C:25]=4[O:24][C:23]4[CH2:22][C:21]([CH3:35])([CH3:34])[CH2:20][C:19](=[O:36])[C:18]3=4)[C:10]=2[CH3:37])=[CH:7][CH:8]=1)#[CH:2].[H][H].ClCCl>CO.[C].[Pd]>[CH2:1]([C:3]1[C:4]([C:38]([OH:40])=[O:39])=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]3[C:30]4[C:29](=[O:31])[CH2:28][C:27]([CH3:32])([CH3:33])[CH2:26][C:25]=4[O:24][C:23]4[CH2:22][C:21]([CH3:34])([CH3:35])[CH2:20][C:19](=[O:36])[C:18]3=4)[C:10]=2[CH3:37])=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 117700766HCID 117700766, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 78324914HCID 78324914, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of the 3-ethynyl-6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylic acid produced in Example 12-3 (100 mg, 0.19 mmol) and 10% palladium carbon (wet) (100 mg) in methanol (2 ml) was prepared at room temperature, and the suspension thus prepared was then stirred at the same temperature as above under a hydrogen atmosphere for 2.5 hours. Thereafter, a solid was removed from the reaction solution by filtration, and the solvent was then distilled away from the filtrate thus obtained under reduced pressure. The residue thus obtained was purified by silica gel thin-layer chromatography (methanol:dichloromethane=1:10, v/v) to obtain the title compound (37.3 mg, yield: 37%).

Workup

  1. customwas prepared at room temperature
  2. customthe suspension thus prepared
  3. customThereafter, a solid was removed from the reaction solution by filtration
  4. distillationthe solvent was then distilled away from the filtrate
  5. customthus obtained under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel thin-layer chromatography (methanol

Sources & evidence

ORD record
ord-283a098a2fb14379a329d9d83c5cbdfe
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

Loading…