Methyl iodide → HCID 59321082, compound

HRID 341210Notes

Reaction equation

HRID 341210 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1)#[CH:2].[N-:27]=[N+:28]=[N-:29].[Na+].IC.O=[C:34]1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.C1COCC1.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:34][N:27]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][N:6]3[C:9]([C:12]4[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=4)=[CH:10][N:11]=[C:5]3[CH:4]=2)[N:29]=[N:28]1

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 33557Sodium AzideHCID 23667548Sodium AscorbateHCID 59320886HCID 59320886, compound

Product 1

HCID 59321082HCID 59321082, compound

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[3-(7-Ethynyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (130 mg, 0.36 mmol) was dissolved in tert-butyl alcohol (2 mL) and water (2 mL). Sodium azide (24 mg, 0.36 mmol) was added, followed by iodomethane (0.18 mL of a 2M solution in THF, 0.36 mmol). The reaction was stirred at room temperature for 5 minutes before the addition of copper (II) sulphate (0.02 mL of a 1M aqueous solution, 0.02 mmol) and sodium ascorbate (7 mg, 0.04 mmol). The reaction was stirred for 2 h at room temperature.

Sources & evidence

ORD record
ord-af8bdc82b5e04e368665e6b4a58f0f8d
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

Loading…