Boron tribromide → HCID 57554982, compound

HRID 1011953Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 99 mg (0.22 mmol) [3-methoxymethyl-5-methyl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (Example 155D]) in 1.8 ml of CH2Cl2 was treated at −30° C. with 0.28 ml BBr3 (1M in dichloromethane, 0.28 mmol). The reaction was warmed up (0° C. for 1 h) and stirred 1.5 h at 0° C. The reaction was treated with saturated NaHCO3-solution. The mixture was extracted with EtOAc (3×), the organic phase was washed with a NaCl solution (10%), dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography over silica gel with CH2Cl2/MeOH 2.5% to 10%, to give 18 mg (19%) of the title compound as light yellow foam. MS: 437.3 (MH+).

Workup

extractionThe mixture was extracted with EtOAc (3×)
washthe organic phase was washed with a NaCl solution (10%)
dry with materialdried (Na2SO4)
customevaporated
customThe crude product was purified by flash chromatography over silica gel with CH2Cl2/MeOH 2.5% to 10%

Sources & evidence

ORD record: ord-f2e8da8d22f24bc4a44b1e5cabef3634
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977358B2

Reaction notes

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