3-Formyl-2-thiopheneboronic Acid (contains varying amounts of Anhydride) → 5-(3-Formyl-thiophen-2-yl)-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-benzoic acid methyl ester

HRID 583367Notes

Reaction equation

HRID 583367 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8](Br)[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[CH:32]([C:34]1[CH:38]=[CH:37][S:36][C:35]=1B(O)O)=[O:33]>>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([C:35]2[S:36][CH:37]=[CH:38][C:34]=2[CH:32]=[O:33])[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 27734293-Formyl-2-thiopheneboronic Acid (contains varying amounts of Anhydride)HCID 70053864HCID 70053864, compound

Product 1

HCID 867543115-(3-Formyl-thiophen-2-yl)-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-benzoic acid methyl esterYield 71%

Procedure

In the same manner as described in Example 241, 505.4 mg (1.0 mmol) of the product of Example 89 and 343.2 mg (2.2 mmol) of 3-formylthiophene-2-boronic acid provided 379 mg (71%) of the desired product as a pale yellow solid. Electrospray Mass Spec 537 (M+H).

Sources & evidence

ORD record
ord-2cf4c740ae544c69875963e68fd9a4c0
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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