Dichloromethane → HCID 58358800, compound

HRID 339739Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:21]2[C:25]([O:26]C)=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:23]([CH3:34])[C:22]=2[CH3:35])=[O:20])[CH2:11][CH2:10]1.B(Br)(Br)Br.C(Cl)Cl>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:21]2[C:25]([OH:26])=[C:24]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:23]([CH3:34])[C:22]=2[CH3:35])=[O:20])[CH2:13][CH2:14]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 25134Boron tribromide

HCID 67319930HCID 67319930, compound

Product 1

HCID 58358800HCID 58358800, compoundYield 24.3%

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl)-4-methoxy-1,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxamide (375 mg, 0.60 mmol) was added BBr3 (0.77 ml, 17% in DCM) slowly at 0° C. After stirring at 0° C. for 2˜3 hours, the mixture was quenched with saturated sodium bicarbonate solution and extracted with DCM (50 mL) MeI (2.13 mL, 34.2 mmol). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by prep HPLC (Gilson, C18 column) to provide title compound (73 mg, 20%).

Workup

customthe mixture was quenched with saturated sodium bicarbonate solution
dry with materialThe organic phase was dried over MgSO4
customevaporated under vacuum
customThe residue was further purified by prep HPLC (Gilson, C18 column)

Sources & evidence

ORD record: ord-0fac4fa5c6ba4bf883a9c63c96cabaa0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895558B2

Reaction notes

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