Ammonium Chloride → (S)-N-(5-bromo-6-(2-(3,5-difluorophenyl)-1-(1,1-dimethylethylsulfinamido)ethyl)pyridin-2-yl)acetamide

HRID 2170309Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH2:5][Mg]Br.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:27][C:28](=[O:30])[CH3:29])=[N:17][C:18]=1[CH:19]=[N:20][S@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22].[Cl-].[NH4+]>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:27][C:28](=[O:30])[CH3:29])=[N:17][C:18]=1[C@@H:19]([NH:20][S:21]([C:23]([CH3:25])([CH3:26])[CH3:24])=[O:22])[CH2:5][C:4]1[CH:3]=[C:2]([F:1])[CH:10]=[C:9]([F:11])[CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(3,5-Difluorobenzyl)magnesium bromide (0.25 M in ether, 10 ml, 2.5 mmol) was added dropwise to a solution of (S)—N-(5-bromo-6-(((tert-butylsulfinyl)imino)methyl)pyridin-2-yl)acetamide (1D, 0.47 g, 1.36 mmol) in DCM (5 ml) at 78° C. The reaction was stirred for 3 h at −78° C. Ammonium chloride (aq, 10 mL) was added to the reaction and the mixture was allowed to warm to r.t. The mixture was extracted with EtOAc (2×30 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product contained a mixture of diastereomers which were used in the next step without further purification. MS (m/z) 474.1 [M+H]+.

Workup

temperatureto warm to r.t
extractionThe mixture was extracted with EtOAc (2×30 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
additiona mixture of diastereomers which
customwere used in the next step without further purification

Sources & evidence

ORD record: ord-eadcb53de8e54fd991aca213f9a598d4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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