Potassium Carbonate → HCID 90459920, compound

HRID 588893Notes

Reaction equation

Br[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20]3)[CH2:15][CH2:14]2)=[O:12])=[C:4]([O:30][CH3:31])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Zn](CC)[CH2:39][CH3:40]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:8][C:7]1[C:2]([CH2:39][CH3:40])=[CH:3][C:4]([O:30][CH3:31])=[C:5]([NH:9][CH2:10][C:11]([N:13]2[CH2:14][CH2:15][N:16]([CH:19]3[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:20]3)[CH2:17][CH2:18]2)=[O:12])[CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of tert-butyl 3-(4-(2-(4-bromo-5-chloro-2-methoxyphenylamino)acetyl)piperazin-1-yl)azetidine-1-carboxylate (100 mg, 0.193 mmol), Pd(dppf)2Cl2 (29 mg, 0.04 mmol) and K2CO3 (55 mg, 0.386 mmol) in DMF (10 mL) at RT, Et2Zn (0.8 mL, 0.8 mmol, 1.0 M in hexane) was added. The resulting mixture was stirred at 80° C. for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1) to afford the crude product (100 mg). ESI-MS m/z: 467.5[M+1]+.

Workup

customThe mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record: ord-df4fa25c61fd4395a5d978ff4924bc5c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227978B2

Reaction notes

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