Potassium Carbonate → HCID 66576755, compound

HRID 1405213Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=2)[N:3]=1.[CH:20]1([O:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2B2OC(C)(C)C(C)(C)O2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[CH:20]1([O:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=3)[N:3]=2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine (134 mg), (Intermediate 1.4), 2-[2-(cyclopropyloxy)-4-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (150 mg; 0.539 mmol) and Pd(dppf)C12 (55 mg; 0.06 mmol) in 1,2-dimethoxyethane (2.0 ml) and 2 M solution of potassium carbonate (0.45 ml) was degassed using argon. The batch was stirred under argon for 1 hour at 100° C. After cooling the batch was diluted with ethyl acetate (35 ml) and THF (35 ml). The organic phase was washed with brine, dried (sodium sulfate) and concentrated. The residue was purified by preparative HPLC to give the desired product (38 mg; 0.12 mmol).

Workup

customwas degassed
temperatureAfter cooling the batch
additionwas diluted with ethyl acetate (35 ml) and THF (35 ml)
washThe organic phase was washed with brine
dry with materialdried (sodium sulfate)
concentrationconcentrated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-e184b7e698194fb580b516ca8c39bf07
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916557B2

Reaction notes

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