Dimethyl Sulfate → N-[2-(5-Chloro-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide

HRID 1262429Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4](I)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.CC1(C)C(C)(C)OB([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH:28][S:29]([CH3:32])(=[O:31])=[O:30])O1.[C:34](=O)([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:28]([CH3:34])[S:29]([CH3:32])(=[O:31])=[O:30])[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2

Participants

Conditions

Temperature: 80 °C

Procedure

5-Chloro-7-iodo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.252 g, 0.774 mmol), N-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide (0.333 g, 1.12 mmol) and Tetrakis(triphenylphosphine)palladium(0) (72 mg, 0.062 mmol) were placed in a vial, followed by N,N-Dimethylformamide (8.0 mL) and 2.00 M of Sodium carbonate in Water (2.00 mL, 4.00 mmol). The sample was partially evacuated, placed under nitrogen and then heated in a 80° C. block for 20 h. Dimethyl sulfate (0.100 mL, 1.06 mmol) was then added to the mixture and heating continued for 7 h. The mixture was then added to water (50 mL) with stirring, portionwise. The resultant ppt was collected, washed with water and dried on the Buchner to afford N-[2-(5-Chloro-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide.

Workup

customThe sample was partially evacuated
temperatureheating
customThe resultant ppt was collected
washwashed with water
customdried on the Buchner

Sources & evidence

ORD record: ord-2b216a6abedd4d1c96e3c2862d3bb029
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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