N-bromobutanimide → HCID 58382028, compound

HRID 1628083Notes

Reaction equation

[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[CH:12][N:11]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[C:8]=3[N:9]=[CH:10][C:5]2=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([OH:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[N:3]=1.C1C(=O)N([Br:41])C(=O)C1>C(Cl)Cl>[Br:41][C:13]1[C:7]2[N:6]3[C:2]([CH3:1])=[N:3][C:4]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([OH:33])([CH3:31])[CH3:32])=[CH:28][CH:29]=4)=[C:5]3[CH:10]=[N:9][C:8]=2[N:11]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:16])[CH3:17])[CH:12]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2-(4-(1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (1.5 g, 3.2 mmol, Preparation #AX.1) in DCM (32.4 ml) at about −20° C. was added NBS (0.46 g, 2.6 mmol). The mixture was stirred at about −20° C. for about 40 min. The mixture was diluted with DCM (100 mL) and washed with saturated aqueous NaHCO3 (75 mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (120 g silica gel column; 0 to 50% EtOAc/heptane) to give 2-(4-(8-bromo-1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.52 g, 29%). LC/MS (Table 2, Method h) Rt=2.51 min; MS m/z 543 (M+H)+.

Workup

washwashed with saturated aqueous NaHCO3 (75 mL)
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (120 g silica gel column; 0 to 50% EtOAc/heptane)

Sources & evidence

ORD record: ord-a4c24d61fa95414c8e9fae82bcd2ba9b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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