Sodium Carbonate → HCID 68153603, compound

HRID 1405418Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8](B(O)O)=[CH:7][CH:6]=[CH:5][N:4]=1.Br[C:13]1[CH:41]=[CH:40][C:16]([C:17]([N:19]2[CH2:39][CH2:38][C:22]3([N:27]([CH3:28])[CH2:26][CH2:25][N:24]4[C:29]([C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])=[CH:30][CH:31]=[C:23]34)[CH2:21][CH2:20]2)=[O:18])=[CH:15][C:14]=1[CH3:42].C([O-])([O-])=O.[Na+].[Na+]>CN1C(=O)CCC1.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:36][C:33]([F:34])([F:35])[C:32]([C:29]1[N:24]2[CH2:25][CH2:26][N:27]([CH3:28])[C:22]3([CH2:38][CH2:39][N:19]([C:17](=[O:18])[C:16]4[CH:40]=[CH:41][C:13]([C:8]5[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=5)=[C:14]([CH3:42])[CH:15]=4)[CH2:20][CH2:21]3)[C:23]2=[CH:31][CH:30]=1)=[O:37]

Participants

Conditions

Temperature: 80 °C

Procedure

To a microtube with Pd(dppf)Cl2 (5.5 mg, 0.075 mmol) was added 2-methoxypyridin-3-ylboronic acid (0.10 mmol) in NMP (0.2 mL), followed by a solution of 1-(1-(4-bromo-3-methylbenzoyl)-2′-methyl-3′,4′-dihydro-2′H-spiro[piperidine-4,1′-pyrrolo[1,2-a]pyrazine]-6′-yl)-2,2,2-trifluoroethanone (0.75 mmol) in DMF (0.3 mL) and aq. Na2CO3 (2M, 4 mmol). The reaction mixture was shaken at 80° C. for 16 h. Filtration followed by purification using preparatory-HPLC (1-99% ACN in water (HCl modifier)) gave 2,2,2-trifluoro-1-[1′-[4-(2-methoxy-3-pyridyl)-3-methyl-benzoyl]-2-methyl-spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-6-yl]ethanone. ESI-MS m/z calc. 526.2, found 527.3 (M+1)+; Retention time: 1.38 minutes (3 min run).

Workup

filtrationFiltration
customfollowed by purification

Sources & evidence

ORD record: ord-1bb9c109d21c4d558188f41d492d1abc
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916565B2

Reaction notes

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