Thiophene-3-boronic acid → Methyl 3-(4-(3-(thiophen-3-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

HRID 534855Notes

Reaction equation

HRID 534855 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[O:15][CH:16]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[S:23]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24]1.S1C=CC=C1C1C=C(C2N=C(CCC(OC)=O)OC=2)C=C(C(F)(F)F)C=1>>[S:23]1[CH:27]=[CH:26][C:25]([C:2]2[CH:3]=[C:4]([C:12]3[N:13]=[C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[O:15][CH:16]=3)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=2)=[CH:24]1

Participants

4

Reactant 3

HCID 581760Thiophene-3-boronic acidHCID 66750877Methyl 3-(4-(3-bromo-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoateHCID 66751326Methyl 3-(4-(3-(thiophen-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

Product 1

HCID 66750869Methyl 3-(4-(3-(thiophen-3-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoateYield 81%

Procedure

The title compound was prepared from methyl 3-(4-(3-bromo-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 44) and thiophene-3-boronic acid by a procedure similar to the one described for methyl 3-(4-(3-(thiophen-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 47) to provide methyl 3-(4-(3-(thiophen-3-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (0.371 g, 81%) as a yellow solid.

Sources & evidence

ORD record
ord-74cf7b37ff3447d5b6668e47508da660
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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