Methanol → 4-(4-Phenylamino-[1,3,5]triazin-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2217182Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:21])=[O:20])[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)=[O:4].Cl[C:32]1[N:37]=[CH:36][N:35]=[C:34]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:33]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)C.C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:20])=[O:21])[CH:7]=[C:8]([C:36]2[N:35]=[C:34]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:33]=[CH:32][N:37]=2)[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

In a 10 mL flask was added 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (1.0 equivalent, 0.34 mmol, 149 mg), (4-chloro-[1,3,5]triazin-2-yl)-phenyl-amine (1.1 equivalent, 0.37 mmol, 78 mg), tetrakistriphenylphosphine palladium (0.2 equivalent, 0.07 mmol, 80 mg), sodium carbonate (1 mL, 2 N), methanol (1 mL) and benzene (5 mL). The resulting mixture was heated at 80° C. for 2 hours then diluted in ethyl acetate and washed with water, brine. The organic layer was dried over sodium sulfate then concentrated under vacuum. The crude mixture was then purified by prep HPLC to afford 55 mg of the title compound. HPLC, Rt=8.8 min, FIA, ES+=478.1.

Workup

washwashed with water, brine
dry with materialThe organic layer was dried over sodium sulfate
concentrationthen concentrated under vacuum
customThe crude mixture was then purified by prep HPLC

Sources & evidence

ORD record: ord-693e2d5d9747448bbd0429d061475fe0
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407962B2

Reaction notes

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