1-Methylhomopiperazine → HCID 86696257, compound
Reaction equation
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.[CH2:43]([O:50][C:51]1[CH:52]=[C:53]2[C:58](=[CH:59][CH:60]=1)[N:57]=[CH:56][C:55](Br)=[CH:54]2)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[CH3:62][N:63]1[CH2:69][CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1.CC([O-])(C)C.[K+]>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]>[CH2:43]([O:50][C:51]1[CH:52]=[C:53]2[C:58](=[CH:59][CH:60]=1)[N:57]=[CH:56][C:55]([N:66]1[CH2:67][CH2:68][CH2:69][N:63]([CH3:62])[CH2:64][CH2:65]1)=[CH:54]2)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
A mixture of Pd2(dba)3 (72.9 mg, 0.080 mmol), xantphos (101 mg, 0.175 mmol), intermediate B (500 mg, 1.591 mmol), 1-methyl-1,4-diazepane (1.1) (182 mg, 1.591 mmol) and KOtBu (357 mg, 3.18 mmol) in toluene (10 ml) was bubbling with nitrogen for 15 min. The reaction was stirred at 110° C. for 3 hr under nitrogen atmosphere. The reaction mixture was filtered and concentrated. The crude product was purified by chromatography to give the title compound (320 mg, yield 58%). LCMS (method N): [M+H]+=348, tR=1.75 min.
Workup
- customwas bubbling with nitrogen for 15 min
- filtrationThe reaction mixture was filtered
- concentrationconcentrated
- customThe crude product was purified by chromatography
Sources & evidence
- ORD record
- ord-1ccda371536d4d03829e1d1a584bc455
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062045B2
Reaction notes
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