Sodium Acetate → HCID 90460208, compound

HRID 588898Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][C:3]=1[CH:11]1[CH2:13][CH2:12]1.[C:14]([N:18]1[CH2:23][CH2:22][N:21]([CH:24]2[CH2:27][N:26]([C:28]([O:30]C(C)(C)C)=O)[CH2:25]2)[CH2:20][CH2:19]1)(=[O:17])[CH:15]=[CH2:16].[C:35]([O-])(=O)[CH3:36].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:28]([N:26]1[CH2:25][CH:24]([N:21]2[CH2:20][CH2:19][N:18]([C:14](=[O:17])/[CH:15]=[CH:16]/[C:5]3[CH:4]=[C:3]([CH:11]4[CH2:13][CH2:12]4)[C:2]([Cl:1])=[CH:7][C:6]=3[O:8][CH3:9])[CH2:23][CH2:22]2)[CH2:27]1)(=[O:30])[CH:35]=[CH2:36]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-chloro-2-cyclopropyl-4-iodo-5-methoxybenzene (300 mg, 0.974 mmol), tert-butyl 3-(4-acryloylpiperazin-1-yl)azetidine-1-carboxylate (431 mg, 1.46 mmol), Pd(OAc)2 (54.6 mg, 0.243 mmol), sodium acetate (239 mg, 2.92 mmol), tetrabutylammonium chloride (539 mg, 1.95 mmol) in DMF (7 mL) was stirred at 100° C. for 24 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to purified by silica gel (dichloromethane/methanol=40:1) to afford the desired product (350 mg, 84% yield). ESI-MS m/z: 476.2[M+H]+.

Workup

customThe mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto purified by silica gel (dichloromethane/methanol=40:1)

Sources & evidence

ORD record: ord-013cdd7b85884441a52c7113d720140f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227978B2

Reaction notes

Loading…