Piperidine → HCID 46909458, compound

HRID 1961422Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C:13]2[C:14]([CH3:23])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][N:17]=3)=[O:12])[CH3:9])=[CH:4][CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:66]1[CH2:71][CH2:70][CH2:69][CH2:68][CH2:67]1>COCCOC.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]>[CH3:23][C:14]1[C:13]([C:11]([NH:10][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([N:66]3[CH2:71][CH2:70][CH2:69][CH2:68][CH2:67]3)=[CH:3][CH:4]=2)[CH3:9])=[O:12])=[CH:22][C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 174 mg (0.47 mmol) (S)—N-(1-(4-bromophenyl)ethyl)-2-methyl-1,8-naphthyridine-3-carboxamide, 11 mg (0.012 mmol) Pd2dba3 and 23 mg (0.048 mmol) XPhos in 3.5 ml DME was stirred an degassed at room temperature for 5 min in a thick walled sealable tube. 250 mg (1.18 mmol) K3PO4 and 52 μl (0.52 mmol) piperidine were added. The tube was sealed and heated at 80° C. over night. The reaction mixture was cooled to room temperature and filtered through a pad of silica with CH2Cl2/MeOH 9:1. The filtrate was concentrated and purified with flash chromatography (SiO2, CH2Cl2/MeOH 30:1) to give 54 mg (31%) of the title compound.

Workup

customan degassed at room temperature for 5 min in a thick walled sealable tube
customThe tube was sealed
temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through a pad of silica with CH2Cl2/MeOH 9:1
concentrationThe filtrate was concentrated
custompurified with flash chromatography (SiO2, CH2Cl2/MeOH 30:1)

Sources & evidence

ORD record: ord-324fe79f9ac542c4b4b5749ab35f75c9
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415333B2

Reaction notes

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