Water → HCID 66893855, compound

HRID 448574Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH:11]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12].O>CN(C=O)C>[CH:11]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([O:23][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])[CH3:12].[CH:11]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([O:23][C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 90 °C

Procedure

2,4-Dichloropyridine (0.52 g, 3.5 mmol) in 2 mL of DMF was added to a suspension of sodium hydride (60% in oil, 0.16 g, 3 eq) and 2a (0.55 g, 3 mmol) in 8 mL of DMF. The mixture was heated at 90° C. The mixture was allowed to cool to room temperature, water was added to quench the excess sodium hydride and the solution was extracted with ethyl acetate twice, washed with a saturated solution of sodium bicarbonate, dried and evaporated. The crude material was purified on silica gel (eluent: 20% then 50% of ethyl acetate in hexane) to give 10a and 10b (0.55 g of the more polar product and 84 mg of the less polar product).

Workup

temperatureto cool to room temperature
customto quench the excess sodium hydride
extractionthe solution was extracted with ethyl acetate twice
washwashed with a saturated solution of sodium bicarbonate
customdried
customevaporated
customThe crude material was purified on silica gel (eluent

Sources & evidence

ORD record: ord-5b1821d060924fab9159672b1d09f748
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481731B2

Reaction notes

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