7-Bromo-4-(2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline → 4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-7-vinyl-quinoline

HRID 8253

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=4)=[N:15][N:14]4[CH2:24][CH2:25][CH2:26][C:13]=34)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:27](C([Sn])=C(CCCC)CCCC)[CH2:28]CC>C1(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>[CH3:23][C:19]1[N:18]=[C:17]([C:16]2[C:12]([C:6]3[C:5]4[C:10](=[CH:11][C:2]([CH:27]=[CH2:28])=[CH:3][CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[C:13]3[CH2:26][CH2:25][CH2:24][N:14]3[N:15]=2)[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Nitrogen is bubbled through a solution of 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline (0.050 g, 0.14 mmol) and tributylvinyltin (0.079 mL, 0.22 mmol) in toluene (2.0 mL) for 20 min. Pd(PPh3)2Cl2 is added and nitrogen bubbled through the reaction mixture for another 10 min. The mixture is heated to 90° C. for 24 h, concentrated in vacuo, and the residue chromatographed on SiO2 (elute with 2% methanol in methylene choloride) to yield the title compound, 0.030 g (61%), as a yellowish solid.

Workup

customnitrogen bubbled through the reaction mixture for another 10 min
concentrationconcentrated in vacuo
customthe residue chromatographed on SiO2 (elute with 2% methanol in methylene choloride)

Sources & evidence

ORD record: ord-c897dfbfc774455391dabcde64d6a518
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Linked notes

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