Sodium Carbonate → HCID 56847069, compound

HRID 570605Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.[Br-].[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[Zn+].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:23]1[C:27]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=4)[N:10]=3)[CH:5]=[CH:6][N:7]=2)=[CH:26][N:25]=[CH:24]1

Participants

Conditions

Temperature: 90 °C

Procedure

8-Chloro-N-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrazin-2-amine (100 mg, 0.319 mmol), 2-thiazolyl zinc bromide (0.5 M in THF, 5 mL, 0.478 mmol), sodium carbonate (2M) (0.24 mL, 0.5 mmol) and tetrakis(triphenyl phosphine) palladium (11 mg, 0.05 mmol) are dissolved and degassed in a mixture of toluene:ethanol (1:1, 4 mL). The reaction mixture is heated 4 hours at 90° C. in a sealed tube. When the reaction is completed, the reaction mixture is cooled down to rt and filtrated through a celite pad and washed with ethyl acetate (10 mL). The filtrate is concentrated and purified by flash chromatography on a silica gel column using (60-120) mesh to get the product as a yellow solid (6.6 mg, 6%); LCMS (method A): mass found (M+H+, 363), Rt (min): 4.50 area % 95.5 (max), 93.5 (254 nm).

Workup

customdegassed in a mixture of toluene:ethanol (1:1, 4 mL)
temperaturethe reaction mixture is cooled down to rt
filtrationfiltrated through a celite pad
washwashed with ethyl acetate (10 mL)
concentrationThe filtrate is concentrated
custompurified by flash chromatography on a silica gel column

Sources & evidence

ORD record: ord-f18e696a8d2b42b7adf8268b365629d3
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023851B2

Reaction notes

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