5-Bromo-1-methyl-1H-imidazole → HCID 86716080, compound
Reaction equation
Br[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][CH:3]=1.CON(C)[C:11]([C:13]1[N:14]=[C:15]([CH3:18])[S:16][CH:17]=1)=[O:12]>C1COCC1>[CH3:7][N:6]1[C:2]([C:11]([C:13]2[N:14]=[C:15]([CH3:18])[S:16][CH:17]=2)=[O:12])=[CH:3][N:4]=[CH:5]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a flask containing 5-bromo-1-methyl-1H-imidazole (345 mg, 2.14 mmol) was added THF (8 mL) and the solution was cooled to 0° C. To this clear homogeneous solution was added isopropylmagnesium chloride-LiCl complex (1.3 M, 2.0 mL, 2.6 mmol) which resulted in a white suspension. The reaction was stirred at 0° C. for 30 min, then a THF (2 mL) solution of N-methoxy-N,2-dimethylthiazole-4-carboxamide (250 mg, 1.34 mmol, Intermediate 38, step a) was introduced and the mixture became more viscous and was allowed to warm to room temperature. After 3 hours the mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (20-40% EtOAc-DCM increasing gradient to 5% MeOH-DCM) provided the title compound as an off-white solid.
Workup
- additionTo this clear homogeneous solution was added isopropylmagnesium chloride-LiCl complex (1.3 M, 2.0 mL, 2.6 mmol) which
- customresulted in a white suspension
- temperatureto warm to room temperature
- customAfter 3 hours the mixture was quenched with saturated NH4Cl solution
- extractionextracted with EtOAc (4×50 mL)
- washThe combined organics were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ab53122419f94d1ba474d010c27c66f6
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309222B2
Reaction notes
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