Sodium Carbonate → 1-[6-(2-Chloro-4-methoxy-5-methyl-phenyl)-5-methyl-pyrazin-2-yl]-1H-benzotriazole

HRID 1593528Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[CH:5]=[N:4][C:3]=1[CH3:17].[Cl:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH3:27])=[CH:21][C:20]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH3:27])=[CH:21][C:20]=1[C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[CH:5]=[N:4][C:3]=1[CH3:17]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of 83 mg 1-(6-Chloro-5-methyl-pyrazin-2-yl)-1H-benzotriazole (0.29 mmol) and 58 mg 2-chloro-4-methoxy-5-methyl-phenyl boronic acid (0.29 mmol) in 0.3 mL toluene was added 0.29 mL 2 M Na2CO3 (aq). After 10 min 10 mg (pbbp)Pd(Cl)2 was added as a solid and the resulting suspension was heated at 110° C. for 16 h. The organic phase was directly subjected to column chromatography eluting with hexane ethyl acetate (0.1% Et3N) to provide the title compound in 50% yield.

Workup

washeluting with hexane ethyl acetate (0.1% Et3N)

Sources & evidence

ORD record: ord-3f49a045fd0245fc9f9961566b6e7079
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297708B2

Reaction notes

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