Dichloromethane → HCID 59232562, compound

HRID 659966Notes

Reaction equation

HRID 659966 reaction equation
[N:1]1([NH:7][C:8]([C:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]#[C:23][CH2:24][OH:25])=[CH:18][CH:17]=3)[N:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])[N:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl>C1COCC1.[Pd]>[N:1]1([NH:7][C:8]([C:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:20][CH:21]=3)[N:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])[N:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 59232565HCID 59232565, compound

Product 1

HCID 59232562HCID 59232562, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a magnetically stirred suspension of 14 mg of palladium (10 wt % on carbon) taken in 8 ml of THF was added compound 2-1 (80 mg, 0.165 mmol) dissolved in 3 ml of THF. The resulting mixture was stirred at room temperature for 2 h under an atmosphere of hydrogen. Then to the mixture was added 10 ml of DCM and the catalyst was filtered and the residue was concentrated and purified by flash column chromatography (petroleum ether-ethyl acetate, 6:4) to afford 61 mg (76%) of 4-1 as a white solid.

Workup

  1. filtrationthe catalyst was filtered
  2. concentrationthe residue was concentrated
  3. custompurified by flash column chromatography (petroleum ether-ethyl acetate, 6:4)

Sources & evidence

ORD record
ord-964dc5455ef04f43af213d704376442c
Source dataset
uspto-grants-2011_12
Patent number
US08084451B2

Reaction notes

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