tert-Butyl piperazine-1-carboxylate → HCID 67466816, compound

HRID 509252Notes

Reaction equation

[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[N:14]=1)[CH2:8]2.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CC(C)([O-])C.[Na+]>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].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>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:13]1[N:14]=[C:15]([N:24]3[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]3)[CH:16]=[CH:17][CH:18]=1)=[O:20])[CH2:8]2

Participants

Conditions

Temperature: 100 °C

Procedure

N-(adamantan-2-yl)-6-bromopicolinamide (80 mg, 0.239 mmol), tert-butyl piperazine-1-carboxylate (49 mg, 0.263 mmol), Pd2(dba)3 (4.4 mg, 0.005 mmol), xantphos (8.3 mg, 0.014 mmol), and sodium-tert-butoxide (34 mg, 0.359 mmol) were suspended in toluene (3 ml), and then stirred at 100° C. under nitrogen stream for 3 hours. The resulting reaction liquid was concentrated under reduced pressure, and then the residue thus obtained was subjected to MPLC (40% EtOAc/Hexanes), to obtain 86.8 mg of pale yellow oil (83%).

Workup

customThe resulting reaction liquid
concentrationwas concentrated under reduced pressure
customthe residue thus obtained

Sources & evidence

ORD record: ord-21eca75012944cd2bf181f503f7c748a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096571B2

Reaction notes

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