Hydrochloric Acid → 2-(2,4-Difluorophenyl)-1-(2-[imidazol-1-yl]pyridin-5-yl)ethanone

HRID 850103Notes

Reaction equation

CON(C)[C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[N:10][CH:11]=1)=[O:5].[F:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[CH2:21][Mg]Br.FC1C=C(F)C=CC=1CBr.[Mg].Cl>C1COCC1.CCOCC>[F:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[CH2:21][C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[N:10][CH:11]=1)=[O:5]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of the product from part (i) (6.5 g, 28 mmol) in THF (100 ml) was stirred under a nitrogen atmosphere at -70° C. and was treated with a solution of 2,4-difluorobenzylmagnesium bromide [from 2,4-difluorobenzyl bromide (8.1 g, 39 mmol) and magnesium (1.0 g, 42 mmol) using the method of Preparation 20(i)] in ether (100 ml). The mixture was stirred at -70° C. for 0.5 hours and was allowed to warm to room temperature before the addition of dilute hydrochloric acid (2N, 100 ml). The layers were separated and the aqueous phase was extracted with dichloromethane (100 ml). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to yield the title compound as a pale yellow solid which was characterised by

Workup

customThe layers were separated
extractionthe aqueous phase was extracted with dichloromethane (100 ml)
dry with materialThe combined organic extracts were dried (MgSO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-3afaf22b410841e881234fb4e890eab5
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015825

Reaction notes

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