Allyl bromide → 1-Allyl-6-chloro-5-iodo-2-methylsulfonyl-imidazo[4,5-b]pyridine
Reaction equation
C(N(CC)C(C)C)(C)C.[CH2:10](Br)[CH:11]=[CH2:12].[Cl:14][C:15]1[CH:16]=[C:17]2[NH:24][C:23]([S:25]([CH3:28])(=[O:27])=[O:26])=[N:22][C:18]2=[N:19][C:20]=1[I:21]>C1COCC1>[CH2:10]([N:24]1[C:17]2[C:18](=[N:19][C:20]([I:21])=[C:15]([Cl:14])[CH:16]=2)[N:22]=[C:23]1[S:25]([CH3:28])(=[O:27])=[O:26])[CH:11]=[CH2:12]Participants
Conditions
- Temperature
- 60 °C
Procedure
N,N-diisopropylethylamine (0.69 ml, 3.95 mmol) and allyl bromide (0.32 ml, 3.70 mmol) were added to a stirred suspension of 6-chloro-5-iodo-2-methylsulfonyl-1H-imidazo[4,5-b]pyridine (1.0824 g, 3.03 mmol) in THF (12.0 ml). The reaction mixture was heated to 60° C. for 18 h, then cooled to room temperature. The reaction mixture was partitioned between EtOAc (50 ml) and brine (50 ml). The organic layer was washed with brine (1×50 ml). The combined aqueous layers were extracted with EtOAc (1×50 ml). The organic layers were combined, dried over Na2SO4, filtered, and evaporated under reduced pressure to give the title compound as a yellow foam. This material was a mixture of the allyl regioisomers and was used without further purification. LC-MS: calculated for C10H9ClIN3O2S 396.91 observed m/e: 397.89 (M+H)+ (Rt 1.12 and 1.17/2 min).
Workup
- temperaturecooled to room temperature
- customThe reaction mixture was partitioned between EtOAc (50 ml) and brine (50 ml)
- washThe organic layer was washed with brine (1×50 ml)
- extractionThe combined aqueous layers were extracted with EtOAc (1×50 ml)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-98b200e600464170b6efd58f26d687d0
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290517B2
Reaction notes
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