Cesium carbonate → 4'-([3-Bromo-4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]thiomethyl)biphenyl-3-sulfonamide

HRID 724681Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[CH:5]=[CH:4][C:3]=1[CH:10]1[S:14](=[O:16])(=[O:15])[NH:13][C:12](=[O:17])[CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].[SH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([S:38]([NH2:41])(=[O:40])=[O:39])[CH:33]=2)=[CH:28][CH:27]=1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[C:10]1[S:14](=[O:16])(=[O:15])[NH:13][C:12](=[O:17])[CH:11]=1)[CH2:8][S:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([S:38]([NH2:41])(=[O:40])=[O:39])[CH:33]=2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 50 mL round bottom flask was placed benzyl bromide of Step 7 (17 mg, 0.045 mmol) and cesium carbonate (0.017 g, 0.054 mmol) under an atmosphere of nitrogen in anhydrous DMF (0.68 mL). The solution was cooled to 0° C., evacuated and refilled with nitrogen several times. 4′-(Mercaptomethyl)biphenyl-3-sulfonamide (15 mg, 0.054 mmol) in 2 mL anhydrous DMF was added to reaction solution dropwise. The resulting solution was stirred at 0° C. for 1 h. The crude material was purified by preparative LCMS to give product as a white solid (4.6 mg 17%). 1H NMR (400 MHz, CD3OD): δ 8.15 (m, 1H), 7.86 (m, 2H), 7.59 (m, 4H), 7.38 (m, 4H), 5.54 (dd, J=18.6, 6.8 Hz, 1H), 3.72 (s, 2H), 3.68 (s, 2H), 3.42 (m, 1H), 3.35 (m, 1H). LCMS found for C23H22BrN2O5S3 (M+H)+: m/z=581, 583.

Workup

customInto a 50 mL round bottom flask was placed
customevacuated
additionrefilled with nitrogen several times
customThe crude material was purified by preparative LCMS

Sources & evidence

ORD record: ord-7302fc0a163f43a6b2be8c5b96df3a38
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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