Potassium Carbonate → HCID 178506233, compound

HRID 387432Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:12][N:13]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1.[C:42]([O-:45])([O-])=[O:43].[K+].[K+]>CN(C=O)C.CO>[F:22][C:21]([F:24])([F:23])[C:42]([OH:45])=[O:43].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:10][C:11]([C:14]3[CH:15]=[CH:16][C:17]([O:20][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[CH:18][CH:19]=3)=[N:12][N:13]=2)=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

Conditions

Temperature: 80 °C

Procedure

4-[5-(4-chloro-3-trifluoromethyl-phenylamino)-4H[1,2,4]triazol-3-yl]-phenol (127.8 mg, 0.36 mmol) was dissolved in 3 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (144.0 mg, 0.72 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 3-bromopyridine (68.3 mg, 0.432 mmol) was added, followed by anhydrous K2CO3 (50.0 mg, 0.36 mmol). Then the vial was capped and microwaved at 250° C. for 30 min. Then the reaction mixture was diluted with ca. 1 mL of MeOH, filtered through 0.22 um syringe filter and purified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA. The product was isolated as a TFA salt (15.1 mg).

Workup

customThen the vial was capped
custommicrowaved at 250° C. for 30 min
filtrationfiltered through 0.22 um syringe
filtrationfilter
custompurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA

Sources & evidence

ORD record: ord-f4ed1f7418394a0e89105f64176707f2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372971B2

Reaction notes

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