Piperidine → HCID 67469042, compound

HRID 1842527Notes

Reaction equation

Br[C:2]1[C:3]([N:8]2[CH2:11][CH:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:74]([O:78][Na])(C)(C)C>O1CCOCC1.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:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH:10]1[CH2:11][N:8]([C:3]2[C:2]([N:22]3[CH2:27][CH2:26][CH:25]([CH2:74][OH:78])[CH2:24][CH2:23]3)=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-[1-(3-bromo-pyridin-2-yl)-azetidin-3-yl]-quinoline (150 mg, 0.51 mmol), piperidine (43.35 mg, 0.51 mmol), BINAP (31.1 mg, 0.05 mmol), t-BuONa (196 mg, 2 mmol) in dioxane (15 mL) was added Pd2(dba)3 (45.75 mg, 0.05 mmol) then the reaction mixture was stirred at 90° C. under a N2 atmosphere overnight. The reaction mixture was filtered through CELITE™ and washed with EtOAc (50 mL). The filtrate was concentrated and the crude product was purified by silica gel column to give [2′-(3-quinolin-2-yl-azetidin-1-yl)-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-yl]-methanol (60 mg, 0.17 mmol, yield 34%).

Workup

filtrationThe reaction mixture was filtered through CELITE™
washwashed with EtOAc (50 mL)
concentrationThe filtrate was concentrated
customthe crude product was purified by silica gel column

Sources & evidence

ORD record: ord-8de995910cfd4347a06a54df38fc3170
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946230B2

Reaction notes

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