Methyl iodide → N-(1,3-Dimethyl-1H-indazol-5-yl)-2-(4-fluoro-phenyl)-2-oxo-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094445Notes

Reaction equation

HRID 1094445 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:34])[C:9]([N:11]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[NH:29][N:28]=[C:27]3[CH3:33])[CH2:12][CH2:13][C:14]2[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:37]I>CN(C=O)C.O.CCOC(C)=O>[CH3:37][N:29]1[C:30]2[C:26](=[CH:25][C:24]([N:11]([CH2:12][CH2:13][C:14]3[CH:15]=[N:16][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:18][CH:19]=3)[C:9](=[O:10])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:34])=[CH:32][CH:31]=2)[C:27]([CH3:33])=[N:28]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178434302HCID 178434302, compound

Product 1

HCID 58007585N-(1,3-Dimethyl-1H-indazol-5-yl)-2-(4-fluoro-phenyl)-2-oxo-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.32 mmol 2-(4-Fluoro-phenyl)-N-(3-methyl-1H-indazol-5-yl)-2-oxo-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide (step 1) in 5 ml dry DMF was added 1.1 eq. NaH and the RM stirred at RT for 30 min. 5 eq. MeI was added and stirring continued for 5 h. Addition of 5 ml H2O, concentration, repartioning between EtOAc and H2O, gave after separation of the layers and concentration the target compound (157 mg) MS(m/e): 485.1 [M+H]+ which was used directly for the next step.

Workup

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  2. customafter separation of the layers and concentration the target compound (157 mg) MS(m/e): 485.1 [M+H]+ which

Sources & evidence

ORD record
ord-3eb90d42da654201a5240bda192014e5
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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