Cesium carbonate → HCID 67326575, compound

HRID 1023332Notes

Reaction equation

I[C:2]1[CH:30]=[CH:29][C:5]([O:6][CH2:7][CH2:8][C:9]2[CH:28]=[CH:27][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:31]1([B-](F)(F)F)[CH2:33][CH2:32]1.[K+].C12(P(C34CC5CC(CC(C5)C3)C4)CCCC)CC3CC(CC(C3)C1)C2.C([O-])([O-])=O.[Cs+].[Cs+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1.O>[CH:31]1([C:2]2[CH:30]=[CH:29][C:5]([O:6][CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][C:12]([CH2:13][N:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:16][CH2:15]4)=[CH:27][CH:28]=3)=[CH:4][CH:3]=2)[CH2:33][CH2:32]1

Participants

Conditions

Temperature: 130 °C

Procedure

tert-Butyl 4-{4-[2-(4-iodophenoxy)ethyl]benzyl}piperazine-1-carboxylate (209 mg), potassium cyclopropyltrifluoroborate (86 mg), Pd(OAc)2 (6 mg), di(1-adamantyl)-n-butyl-phosphine (13 mg), Cs2CO3 (391 mg), and toluene/water (10:1) (3.3 mL) were mixed in a 5 mL process vial. The vial was sealed, and the reaction mixture was heated with microwaves to 130° C. for 1 hour. After filtration through a Celite pad, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/0 to 0/1) to give tert-butyl 4-{4-[2-(4-cyclopropylphenoxy)ethyl]benzyl}piperazine-1-carboxylate as a pale yellow solid (40 mg).

Workup

customThe vial was sealed
filtrationAfter filtration through a Celite pad
customthe solvent was removed under reduced pressure
customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/0 to 0/1)

Sources & evidence

ORD record: ord-5d02b3249fd3490f98719c1a3f298fcc
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722663B2

Reaction notes

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