Piperidine → HCID 58911012, compound
Reaction equation
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[CH:53]=[CH:52][C:51]([N:54]([C:63]2[S:64][CH:65]=[C:66]([C:68]3[CH:73]=[CH:72][C:71]([N:74]4[CH:78]=[CH:77][N:76]=[CH:75]4)=[CH:70][CH:69]=3)[N:67]=2)COCC[Si](C)(C)C)=[CH:50][CH:49]=1.[NH:79]1[CH2:84][CH2:83][CH2:82][CH2:81][CH2:80]1.CC([O-])(C)C.[Na+]>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]>[N:74]1([C:71]2[CH:70]=[CH:69][C:68]([C:66]3[N:67]=[C:63]([NH:54][C:51]4[CH:52]=[CH:53][C:48]([N:79]5[CH2:84][CH2:83][CH2:82][CH2:81][CH2:80]5)=[CH:49][CH:50]=4)[S:64][CH:65]=3)=[CH:73][CH:72]=2)[CH:78]=[CH:77][N:76]=[CH:75]1Participants
7
Procedure
In a heat-gun dried vial that was purged with nitrogen, (+/−)-BINAP (10 mg, 0.015 mmol) was dissolved in anhydrous toluene (1 mL). After 2 minutes, Pd2(dba)3 (3 mg, 0.0025 mmol), compound 1208 (53 mg, 0.1 mmol), and piperidine (11 mg, 0.12 mmol) were added to the reaction flask. After stirring at room temperature for 5 minutes, NaOtBu (14 mg, 0.14 mmol) was added and the reaction mixture was heated at 90° C. for 18 hours before passage through a 0.45 μm filter and subsequent HPLC purification. Compound 1209 was isolated as a brown oil (1.3 mg). Expected mass spectrometry=401; observed=402 [M+1].
Workup
- customIn a heat-gun dried vial
- temperaturethe reaction mixture was heated at 90° C. for 18 hours before passage through a 0.45 μm
- filtrationfilter
- customsubsequent HPLC purification
Sources & evidence
- ORD record
- ord-cb33a641c15e438d862e01019a0edfd6
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119680B2
Reaction notes
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