Sodium Carbonate → Propane-2-sulfonic acid {2-[4'-(2-hydroxy-ethyl)-biphenyl-4-yl]-thiophen-3-yl}amide

HRID 746781

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:11][CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][OH:43])=[CH:37][CH:36]=1>COCCOC.CCO>[OH:43][CH2:42][CH2:41][C:38]1[CH:39]=[CH:40][C:35]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:22])=[O:23])=[CH:13][CH:14]=2)=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 92.5 °C

Procedure

Mix propane-2-sulfonic acid{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide (0.10 g), 0.1 equiv of tetrakis triphenylphosphine palladium (0), 2 equiv of 2M sodium carbonate aqueous solution in DME (2 mL) and EtOH(1 mL) and warm to 90-95° C. After warming two min, add 2-(4-bromo-phenyl)-ethanol (1.3 equiv) and stir at that temperature for 1.5 h. Evaporate solvents over Celite® and purify by silica gel Strata® cartridges eluting with hexanes-EtOAc gradient to give 0.041 g of the title compound. MS (ES+) (m/z): 402 (M+1).

Workup

temperatureAfter warming two min
customEvaporate solvents over Celite® and purify by silica gel Strata® cartridges
washeluting with hexanes-EtOAc gradient

Sources & evidence

ORD record: ord-97b0e8c9c2a14cf698b75686a82e6caa
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393868B2

Linked notes

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