Cesium carbonate → HCID 86654352, compound

HRID 339689Notes

Reaction equation

[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13](Br)[CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[NH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24][CH2:23]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:32]([O:31][C:30](=[O:36])[NH:29][CH2:28][CH:25]1[CH2:24][CH2:23][N:22]([C:13]2[CH:14]=[C:15]([F:20])[CH:16]=[C:17]3[C:12]=2[N:11]=[C:10]([C:3]2[N:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[N:1][N:2]=2)[CH:19]=[CH:18]3)[CH2:27][CH2:26]1)([CH3:35])([CH3:33])[CH3:34]

Participants

Conditions

Temperature: 95 °C

Procedure

2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-bromo-6-fluoroquinoline (70 mg, 0.20 mmol), tert-butyl piperidin-4-ylmethylcarbamate (56.8 mg, 0.27 mmol), and Cs2CO3 (66 mg, 0.20 mmol) were weighed into a 5.0 mL reaction vial and suspended in 2.0 mL of anhydrous toluene. The solution was purged with Argon followed by addition of Pd2dba3 (93.4 mg, 0.10 mmol), Binap-rac (12.7 mg, 0.020 mmol), then heated to 95° C. for 48 hours. The reaction was cooled to ambient temperature, followed by filtration through a celite plug to remove catalyst. The crude reaction was concentrated in vacuo and used without further purification (97 mg, 97% yield). MS APCI (+) m/z 477 (M+1) detected.

Workup

customThe solution was purged with Argon
temperatureThe reaction was cooled to ambient temperature
filtrationfollowed by filtration through a celite plug
customto remove catalyst
customThe crude reaction
concentrationwas concentrated in vacuo
customused without further purification (97 mg, 97% yield)

Sources & evidence

ORD record: ord-b7779a00d93b4d03b2dda4ef65c64072
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895550B2

Reaction notes

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