2-Thiopheneboronic acid → N-(indan-5-yl)-5-nitro-2-thiophen-2-yl-benzamide

HRID 1531277Notes

Reaction equation

HRID 1531277 reaction equation
C(NC1CC2C(=CC=C(NC(C3C(C4C=CC(F)=CC=4)=CC=CC=3)=O)C=2)C1)(=O)C.Br[C:31]1[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][C:32]=1[C:33]([NH:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[CH2:41][CH2:40][CH2:39]2)=[O:34].[S:52]1[CH:56]=[CH:55][CH:54]=[C:53]1B(O)O>>[CH2:41]1[C:42]2[C:38](=[CH:37][C:36]([NH:35][C:33](=[O:34])[C:32]3[CH:45]=[C:46]([N+:49]([O-:51])=[O:50])[CH:47]=[CH:48][C:31]=3[C:53]3[S:52][CH:56]=[CH:55][CH:54]=3)=[CH:44][CH:43]=2)[CH2:39][CH2:40]1

Participants

4

Reactant 3

HCID 27339602-Thiopheneboronic acidHCID 212533662-Bromo-N-indan-5-yl-5-nitro-benzamideHCID 543765954'-Fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide

Product 1

HCID 21253368N-(indan-5-yl)-5-nitro-2-thiophen-2-yl-benzamide

Procedure

N-(Indan-5-yl)-5-nitro-2-(thiophen-2-yl)-benzamide is prepared similarly to the title compound of Example 3 using the title B compound, 2-bromo-N-(indan-5-yl)-5-nitro-benzamide (0.137 g, 0.380 mmol) and 2-thiopheneboronic acid (0.073 9, 0.570 mmol). 1H NMR (DMSO-d6, 300 MHz): δ 10.59 (1H, s), 8.38 (1H, dd), 8.30 (1H, d), 7.81 (1H, d), 7.73 (1H, d), 7.06 (1H, s), 7.46 (1H, d), 7.30 (1H, d), 7.18 (2H, m), 2.83 (4H, q), 2.01 (2H, m).

Sources & evidence

ORD record
ord-002dfe8d1c31491cac74d389668c0fa6
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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