Cyclobutylamine → HCID 57691120, compound
Reaction equation
CC(C)([O-])C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:50]1[CH:51]=[C:52]2[C:58]([C:59]([F:71])([F:70])[C:60]3[CH:61]=[C:62]4[C:67](=[CH:68][CH:69]=3)[N:66]=[CH:65][CH:64]=[CH:63]4)=[N:57][O:56][C:53]2=[N:54][CH:55]=1.[CH:72]1([NH2:76])[CH2:75][CH2:74][CH2:73]1>C1(C)C=CC=CC=1.ClCCl.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]>[CH:72]1([NH:76][C:50]2[CH:51]=[C:52]3[C:58]([C:59]([F:71])([F:70])[C:60]4[CH:61]=[C:62]5[C:67](=[CH:68][CH:69]=4)[N:66]=[CH:65][CH:64]=[CH:63]5)=[N:57][O:56][C:53]3=[N:54][CH:55]=2)[CH2:75][CH2:74][CH2:73]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a pressure vial was added sodium tert-butoxide (38 mg, 0.40 mmol), xantphos (0.12 g, 0.20 mmol), Pd2(dba)3 (61 mg, 0.066 mmol), 6-((5-bromoisoxazolo[5,4-b]pyridin-3-yl)difluoromethyl)quinoline (0.10 g, 0.27 mmol), and cyclobutanamine (0.025 mL, 0.29 mmol) in toluene (3 mL). The mixture was stirred at 80° C. for two hours then was diluted with dichloromethane and filtered through celite. Purification of the filtrate by MPLC (eluted with a gradient of 10 to 50% ethyl acetate in hexanes) afforded the product as a yellow oil (5.1 mg, 5%). MS m/z=367.0 [M+1]+ Calc'd for C20H16F2N4O: 366.4
Workup
- filtrationfiltered through celite
- customPurification of the filtrate by MPLC (
- washeluted with a gradient of 10 to 50% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-a6c4d6ed57414a5781e682ebf5452713
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198448B2
Reaction notes
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