O-Xylene → HCID 23130722, compound

HRID 2080224Notes

Reaction equation

[NH2:1][C:2]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].[CH:25]1C=CC(CC(NCN[C@H](C(O)=O)CC2C=CC([N+]([O-])=O)=CC=2)=O)=C[CH:26]=1.C1(C)C(C)=CC=CC=1.C([Sn](CCCC)(CCCC)CCCC)=C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[NH2:1][C:2]1[N:23]=[C:22]([CH:25]=[CH2:26])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

Conditions

Temperature: 130 °C

Procedure

To a mixture of 2-amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (30 mg, 0.083 mmol), tetrakis(triphenylphosphine)palladium(0) (19 mg, 0.017 mmol) and xylene (1.5 mL) was added vinyl(tri-butyl)tin (0.073 mL, 0.25 mmol), and the solution was stirred at 130° C. for 3 hours. After cooling, water and ethyl acetate were added to the reaction solution for extraction, which was then washed with brine. The solvent was evaporated in vacuo, then, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (19 mg, 0.054 mmol, 65%) was obtained as a white solid.

Workup

temperatureAfter cooling
washwas then washed with brine
customThe solvent was evaporated in vacuo
customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-f98b57a4467d4444848b6ba99589ad74
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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