Cesium carbonate → (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxyphenyl)amino)phenyl)acrylate

HRID 1504417Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([O:9][CH3:10])[CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][C:13]=1/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+].C1(OC)CCCC1>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.O>[CH2:19]([S:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[O:9][CH3:10])=[C:13](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:14]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A RBF charged with xantphos (9.97 g, 17.23 mmol), pd2(dba)3 (5.26 g, 5.74 mmol), 4-bromo-1-iodo-2-methoxybenzene (74.9 g, 239 mmol), (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (60.000 g, 191 mmol), cesium carbonate (100 g, 306 mmol), and 400 ml cylopentyl-methylether was heated to 90° C. overnight. The reaction mixture was then poured into water and extracted with DCM. The organics were dried over MgSO4 and concentrated. The crude residue was triturated with IPA leaving a yellow solid that was collected and dried (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxyphenyl)amino)phenyl)acrylate (86.95 g, 174 mmol, 91% yield). m/z (ESI) 500.1 (M+H)+.

Workup

extractionextracted with DCM
dry with materialThe organics were dried over MgSO4
concentrationconcentrated
customThe crude residue was triturated with IPA leaving a yellow solid
customthat was collected

Sources & evidence

ORD record: ord-ea03c5bf2b68478e83fade73c4e31fe8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

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