HCID 59571690, compound → HCID 42613946, compound

HRID 1043029Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

N-(2-([2-(4-Chloro-phenoxy)-phenylimino]-methyl)-phenyl)-acetamide (111 mg, assumed 100% pure, 0.3 mmol) was dissolved in THF (5 ml) and cooled to 0° C. under a N2 atmosphere, to this was added BF3OEt2 (0.04 ml, 0.3 mmol) and benzylmagnesium bromide (2 M in THF, 0.3 ml, 1.2 mmol). The resulting solution was stirred at r.t. for 18 h. The reaction was then quenched with sat. NH4Cl solution, extracted with EtOAc and dried (MgSO4). The crude product was purified by flash chromatography (0-20% EtOAc in DCM) to yield the desired product, 20 mg, 14% yield.

Workup

customThe reaction was then quenched with sat. NH4Cl solution
extractionextracted with EtOAc
dry with materialdried (MgSO4)
customThe crude product was purified by flash chromatography (0-20% EtOAc in DCM)

Sources & evidence

ORD record: ord-c4c1216110e34a0e9a13db8e9f4b9e6d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08558028B2

Reaction notes

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