Trimethylsilyl triflate → HCID 90410971, compound

HRID 2177644Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[N:10]=[N:9]2)[N:3]=1.[Cl:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].F[C:32](F)(F)S(O[Si](C)(C)C)(=O)=O.C[Mg+].[Br-]>C1COCC1>[Cl:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:13]1[CH:14]=[CH:15][C:16]2[N:8]([C:4]3[N:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=3)[N:9]=[N:10][C:11]=2[CH:12]1[CH3:32])=[O:21]

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of the product of Example 252, Step 1 (200 mg, 0.94 mmol) in THF (30 mL) cooled to −78° C. was added Intermediate 12 (251 mg, 1.04 mmol). Trimethylsilyl trifluoromethanesulfonate (0.188 mL, 1.04 mmol) was then added and the reaction was stirred at −78° C. for 30 min. The resulting mixture was treated with MeMgBr (3.0 M solution in Et2O, 0.94 mL, 2.83 mmol) and stirred for 1 h. The reaction was quenched with NH4Cl and extracted with EtOAc, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel (0-5% MeOH/DCM) to provide the desired product (66 mg, 16%). MS (ESI) mass calcd. C19H14ClF3N6O, 434.1. m/z found, 435.1 [M+H]+.

Workup

stirringstirred for 1 h
customThe reaction was quenched with NH4Cl
extractionextracted with EtOAc
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by chromatography on silica gel (0-5% MeOH/DCM)

Sources & evidence

ORD record: ord-f5844f0a188a4dbcbe3ce760b25126cb
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09066946B2

Reaction notes

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