Pyridine → Ethyl 3-(((benzyloxy)carbonyl)amino)-7-bromoquinoline-2-carboxylate

HRID 924364Notes

Reaction equation

N1C=CC=CC=1.[NH2:7][C:8]1[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Br:18])[CH:12]=2.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C(Cl)Cl.CCOC(C)=O>[CH2:28]([O:27][C:25]([NH:7][C:8]1[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Br:18])[CH:12]=2)=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Pyridine (727.5 mg, 9.197 mmol) was added to a solution of ethyl 3-amino-7-bromoquinoline-2-carboxylate (Ark Pharm, 1069 mg, 3.622 mmol) in DCM (10.0 mL). The mixture was cooled to −10° C. A solution of benzyl chloroformate (816.5 mg, 4.547 mmol) in DCM (5.0 mL) was added slowly to the solution. The reaction mixture was allowed to warm to room temperature. After stirring at room temperature for 1 h, the reaction mixture was diluted with EtOAc (100 mL), washed with a saturated aqueous solution of NaHCO3 (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (0-50% EtOAc in hexanes) to give the sub-title compound as an off-white solid (1.54 g, 99%). LCMS calc. for C20H18BrN2O4(M+H)+: m/z=429.0. found 429.0.

Workup

temperatureto warm to room temperature
washwashed with a saturated aqueous solution of NaHCO3 (100 mL), brine (100 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by flash chromatography on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-1c7f20e735d74f8db8e3366a2f753ebe
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278950B2

Reaction notes

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