N-(4-bromo-2-methylphenyl)methanesulfonamide → HCID 86689543, compound

HRID 1853807Notes

Reaction equation

HRID 1853807 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([CH3:13])[CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:33]1[C:34]2[C:35]3[CH:48]=[CH:47][S:46][C:36]=3[C:37](=[O:45])[NH:38][C:39]=2[CH:40]=[CH:41][C:42]=1[O:43][CH3:44]>>[CH3:44][O:43][C:42]1[CH:41]=[CH:40][C:39]2[NH:38][C:37](=[O:45])[C:36]3[S:46][CH:47]=[CH:48][C:35]=3[C:34]=2[C:33]=1[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 669156N-(4-bromo-2-methylphenyl)methanesulfonamideHCID 2733548Bis(pinacolato)diboraneHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 86689543HCID 86689543, compoundYield 27.3%

Procedure

Following General Procedure E, N-(4-bromo-2-methylphenyl)methanesulfonamide (130 mg, 0.50 mmol) was reacted with bis(pinacolato)diboron (140 mg, 0.55 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.45 mmol) to afford the desired product (51 mg, 27%) as a brown solid: ESI MS m/z 415 [C20H18N2O4S2+H]+.

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-8b9bb8d07536402c81f99a28dfb6b05c
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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