Sodium Bicarbonate → HCID 86271308, compound

HRID 2177590Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[N:7]1[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:9]=[N:8]1.[Cl:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].C[Mg+].[Br-].[C:33]([O-])(O)=O.[Na+]>C1COCC1>[Cl:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([N:12]1[CH:13]=[CH:14][C:15]2[N:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)[N:8]=[N:9][C:10]=2[CH:11]1[CH3:33])=[O:20]

Participants

Conditions

Temperature: 23 °C

Procedure

A suspension of 1-pyrazin-2-yl-1H-[1,2,3]triazolo[4,5-c]pyridine (100 mg, 0.5 mmol) in THF (2.5 mL) was treated with 2-chloro-3-(trifluoromethyl)benzoyl chloride (135 mg, 0.56 mmol) and the reaction stirred for 10 min at 23° C. The reaction was cooled to −50° C. and treated with MeMgBr (3.0 M solution in Et2O, 0.18 mL, 0.56 mmol), and reaction slowly warmed to 23° C. over 30 minutes. Saturated NaHCO3 solution was added to the reaction mixture, which was then extracted with EtOAc and purified on 16 g SiO2 with 0-50% ethyl acetatehexanes to provide 174 mg (82%) of 5-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-4-methyl-1-pyrazin-2-yl-4,5-dihydro-1H-[1,2,3]triazolo[4,5-c]pyridine. MS (ESI): mass calcd. for C18H12ClF3N6O, 420.1. m/z found, 421.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.64-9.45 (t, J=1.8 Hz, 1H), 8.75-8.58 (d, J=2.6 Hz, 1H), 8.51-8.38 (ddd, J=6.8, 2.6, 1.5 Hz, 1H), 7.95-7.78 (dt, J=4.5, 1.8 Hz, 1H), 7.70-7.38 (m, 2H), 6.69-6.54 (m, 1H), 6.44-6.22 (m, 2H), 1.70-1.50 (m, 4H).

Workup

temperatureThe reaction was cooled to −50° C.
temperatureslowly warmed to 23° C. over 30 minutes
extractionwas then extracted with EtOAc
custompurified on 16 g SiO2 with 0-50% ethyl acetatehexanes

Sources & evidence

ORD record: ord-ec5bef20cd404b8b9d88f483db2d6128
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09066946B2

Reaction notes

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