Benzyl methyl(piperidin-4-yl)carbamate → HCID 66798915, compound

HRID 1193374Notes

Reaction equation

[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([N:26]([CH3:28])[CH3:27])[CH:21]=1.C(O[Na])(C)(C)C>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]>[CH3:27][N:26]([CH3:28])[C:22]1[CH:21]=[C:20]([N:16]2[CH2:15][CH2:14][CH:13]([N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:18][CH2:17]2)[CH:25]=[CH:24][N:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Benzyl methyl(piperidin-4-yl)carbamate (0.862 mmol, 1.0 eq.), 4-bromo-N,N-dimethylpyridin-2-amine (173 mg, 0.862 mmol, 1.0 eq.) and t-BuONa (193 mg, 1.72 mmol, 2.0 eq.) were taken up in toluene (10 ml) and degassed with N2. BI NAP (26 mg, 0.043 mmol, 0.05 eq.) and Pd2(dba)3 (39 mg, 0.043 mmol, 0.05 eq.) were then added and the mixture was heated for 16 hours at 80° C. After monitoring by TLC, the reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, 4% MeOH in DCM). Yield: 63% (200 mg, 03543 mmol)

Workup

customdegassed with N2
filtrationthe reaction mixture was filtered over Celite
concentrationthe filtrate was concentrated under reduced pressure
custompurified by column chromatography (silica gel, 4% MeOH in DCM)

Sources & evidence

ORD record: ord-58f8839a0e654266bef0d0c725e3e777
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680159B2

Reaction notes

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