N-bromobutanimide → [3-Bromo-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester

HRID 420494Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[CH:23]=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:34])C(=O)C1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([Br:34])=[CH:24][N:25]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of [6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester (543 mg, 1.38 mmol) in DMF (5 mL) was cooled to 0° C., treated with NBS (222 mg, 1.25 mmol), and stirred at 0° C. for 1 h. The reaction mixture was diluted in AcOEt and washed with water and brine. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→6:4) to yield the title compound (435 mg, 0.92 mmol, 67%) as a beige foam. MS: 472 [M+1]+; HPLC: AtRet=1.93; TLC: RF 0.50 (hexane/DCM/TBME 1:1:2).

Workup

washwashed with water and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→6:4)

Sources & evidence

ORD record: ord-d09b885e10f842ccb174302c4aab43ba
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097617B2

Reaction notes

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