2-Thiopheneboronic acid → HCID 67222388, compound

HRID 876611Notes

Reaction equation

HRID 876611 reaction equation
[OH:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=2)[C:11]1=[O:23])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:24][C:25]([O:28][C:29]([N:31]1[CH:35]=[CH:34][C:33](B2OC(C)(C)C(C)(C)O2)=[N:32]1)=[O:30])([CH3:27])[CH3:26].S1C=CC=C1B(O)O>>[C:6]([O:5][C:3](=[O:4])[C@@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:17]=[C:18]([C:34]3[CH:33]=[N:32][N:31]([C:29]([O:28][C:25]([CH3:27])([CH3:26])[CH3:24])=[O:30])[CH:35]=3)[CH:19]=[CH:20][CH:21]=2)[C:11]1=[O:23])[OH:1])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 27339602-Thiopheneboronic acidHCID 46705337tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 67223356HCID 67223356, compound

Product 1

HCID 67222388HCID 67222388, compoundYield 62.7%

Procedure

According to the Step 22-1 in synthetic method for EXAMPLE 22, compound 107-1 (0.2 g) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylic acid 1,1-dimethylethyl ester (0.27 g) were used instead of 14-4 and 2-thiopheneboronic acid to obtain compound 107-2 (137 mg) as a pale yellow amorphous solid.

Sources & evidence

ORD record
ord-d920ecf4ce1e46049b9bdbb5dca40dcc
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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