Trimethyl borate → HCID 117840112, compound

HRID 1477723Notes

Reaction equation

O1CCOC[CH2:2]1.Br[C:8]1[CH:9]=[C:10]([CH2:17][N:18]2[CH:23]=[N:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=[N:20][C:19]2=[O:37])[S:11][C:12]=1[C:13]([F:16])([F:15])[F:14].B(OC)(OC)OC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[F:36][C:33]1[CH:34]=[CH:35][C:30]([N:27]2[CH2:28][CH2:29][N:24]([C:21]3[N:22]=[CH:23][N:18]([CH2:17][C:10]4[S:11][C:12]([C:13]([F:16])([F:15])[F:14])=[C:8]([CH3:2])[CH:9]=4)[C:19](=[O:37])[N:20]=3)[CH2:25][CH2:26]2)=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 1,4-dioxane (2.0 mL)-water (0.25 mL) solution of 1-{[4-bromo-5-(trifluoromethyl)thiophen-2-yl]methyl}-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (50.9 mg, 0.0982 mmol) synthesized in Synthesis Example 154, tetrakis(triphenylphosphine)palladium (0) (11.6 mg, 0.0100 mmol), trimethyl borate (41 μL, 0.295 mmol), and sodium carbonate (20.8 mg, 0.196 mmol) was stirred in nitrogen atmosphere at 100° C. for 3 hours. After the completion of the reaction, to the reaction solution, water was added and a deposited solid was smeared on silica gel. The resultant mixture was eluted with ethyl acetate and the resultant eluate was concentrated under reduced pressure. The resultant solid was purified by silica gel column chromatography to obtain the title compound (5.82 mg, yield: 13%).

Workup

customAfter the completion of the reaction
washThe resultant mixture was eluted with ethyl acetate
concentrationthe resultant eluate was concentrated under reduced pressure
customThe resultant solid was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-3f0f4f6482e64c649bcec5b08999508a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403798B2

Reaction notes

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