Tributylvinyltin → 2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-vinylimidazo[4,5-b]pyridine

HRID 396372Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13](Cl)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.[CH:30]([Sn](CCCC)(CCCC)CCCC)=[CH2:31]>C1(C)C(C)=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13]([CH:30]=[CH2:31])=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

2-(4-Fluorophenyl)-1-(2-cyclopentylamino-4-pyrimidinyl)-5-chloroimidazo[4,5-b]pyridine (50 mg 0.12 mmol), vinyltributylstannane (4.3 ml 0.15 mmol) and PdCl2(PPh3)2 (8.6 mg 0.01 mmol) are dissolved in xylene (1 ml) and heated to 160° C. for 1 h under argon. The reaction mixture is purified over SiO2 (acetone/hexanes 15/85) to yield the title compound as colorless crystals (42 mg 86%)

Workup

customThe reaction mixture is purified over SiO2 (acetone/hexanes 15/85)

Sources & evidence

ORD record: ord-fc813a0ea39c43709d727a5df67106ae
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608072B1

Reaction notes

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