Phenyl chloroformate → HCID 57590875, compound

HRID 1783764Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:10]1([O:16][C:17](Cl)=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br-].[CH2:21]([Zn+])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>C1COCC1>[CH2:21]([CH:9]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:17]([O:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])[CH:3]=[C:2]1[Br:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-bromonicotinaldehyde (7-1) (930 mg, 5 mmol, 1 eq) in anhydrous THF (10 ml) was cooled to 0° C. and treated with phenylchloroformate (783 mg, 5 mmol, 1eq). The reaction mixture was then stirred at this temperature for 1 h before the addition of benzylzinc bromide (0.5M in THF, 10 ml, 5 mmol, 1eq). The resulting solution was stirred at 0° C. for another 30 min, was then allowed to warm to room temperature and poured into saturated aqueous solution of ammonium chloride. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate, the combined organic extracts were dried and concentrated to give the title dyhydropyridine 7-2, which was used in the next step without further purification. LRMS m/z: found 398.0, 400.0, calcd. (M+H) 398.0, 400.0

Workup

temperatureto warm to room temperature
customThe organic layer was separated
extractionthe aqueous layer was extracted three times with ethyl acetate
customthe combined organic extracts were dried
concentrationconcentrated
customto give the title dyhydropyridine 7-2, which
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-fafcb209e0344b24b1ded107304c4640
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501435B2

Reaction notes

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