Piperazine → HCID 57832789, compound

HRID 729497Notes

Reaction equation

Br[C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[NH:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1>C1(C)C=CC=CC=1>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:3]3[C:2]([N:48]4[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]4)=[CH:7][CH:6]=[CH:5][N:4]3[CH:8]=2)=[CH:12][CH:13]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 115 °C

Procedure

To a flask containing 8-bromo-2-(4-tert-butyl-phenyl)-imidazo[1,2-a]pyridine (0.313 g, 0.951 mmol) was added tris(dibenzylidineacetone)dipalladium(0) (0.087 g, 0.0.0951 mmol), 2-(di-tert-butylphosphino)biphenyl (0.028 g, 0.0951 mmol), sodium tert-butoxide (0.183 g, 1.90 mmol) and piperazine (0.409 g, 4.76 mmol). The solid reagents were then suspended in degassed toluene (22 mL). The mixture was purged with nitrogen and heated to 115° C. for 2 h. The reaction mixture was concentrated to dryness under reduced pressure. The crude mixture was purified by flash silica gel chromatography, eluting with 15% methanol/chloroform to give 0.242 g (76%) of the title compound. MS (ES) m/z 335.1; HPLC (Method B): r.t.=8.4 min., purity 98.6% at 210-370 nm. HRMS: calcd for C21H26N4+H+, 335.22302; found (ESI, M+H), 335.2236.

Workup

customThe mixture was purged with nitrogen
concentrationThe reaction mixture was concentrated to dryness under reduced pressure
customThe crude mixture was purified by flash silica gel chromatography
washeluting with 15% methanol/chloroform

Sources & evidence

ORD record: ord-e843d2d351a744d6906e8f07764ccb4d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582636B2

Reaction notes

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