Nitrogen → 6-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)-3-(4-methylpiperazin-1-yl)quinoline

HRID 2175159Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([SH:11])=[N:9][N:10]=2)[CH:7]=1.C[C:13]1(C)[C:39]2[C:34](=[C:35](P(C3C=CC=CC=3)C3C=CC=CC=3)[CH:36]=[CH:37][CH:38]=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=[CH:19][C:14]1=2.C[CH2:55][N:56]([CH:60](C)C)C(C)C.[N:63]#N.[CH3:65][N:66]([CH:68]=O)[CH3:67]>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]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][C:37]3[CH:38]=[C:39]4[C:34](=[CH:35][CH:36]=3)[N:63]=[CH:19][C:14]([N:56]3[CH2:60][CH2:68][N:66]([CH3:67])[CH2:65][CH2:55]3)=[CH:13]4)=[N:9][N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of Intermediate I (138 mg, 0.599 mmol), Intermediate Q14 (150 mg, 0.4 mmol), Pd2(dba)3 (36.6 mg, 0.04 mmol), xantphos (46.2 mg, 0.08 mmol) and DIPEA (0.14 ml, 0.799 mmol) in DMF (6 ml) was bubbled by N2 for 10 min, and then heated at 100° C. for 4 hours in oil bath. The reaction mixture was quenched with water and extracted with EtOAc for three times. The combined extract was washed with brine and dried over anhydrous Na2SO4. Solvent was evaporated and the residue was purified by silica gel chromatography to afford the title compound (0.08 g, 44% yield). LCMS (method A): [M+H]+=455/457, tR=1.7 min.

Workup

customThe reaction mixture was quenched with water
extractionextracted with EtOAc for three times
extractionThe combined extract
washwas washed with brine
dry with materialdried over anhydrous Na2SO4
customSolvent was evaporated
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-1a9f2b89f3224747a07fb0eda41243a4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062045B2

Reaction notes

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