Ethanol → 3-(3-Hydroxymethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 659670Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[CH2:10]([C:14]1[S:18][C:17]([S:19]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])=[O:20])=[C:16](B(O)O)[CH:15]=1)[CH:11]([CH3:13])[CH3:12].[OH-].[Na+].CCO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([C:16]2[CH:15]=[C:14]([CH2:10][CH:11]([CH3:12])[CH3:13])[S:18][C:17]=2[S:19]([NH:22][C:23]([CH3:25])([CH3:24])[CH3:26])(=[O:21])=[O:20])[CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of m-bromobenzyl alcohol (1.05 g, 5.80 mmol), 5-iso-butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (2.41 g, 7.55 mmol; see step (c)), Pd(PPh3)4 (270 mg, 0.235 mmol), NaOH (19.1 mL, 1.5 M aq, 28.6 mmol), EtOH (5.0 mL) and toluene (30 mL) was stirred under N2 at 90° C. for about 4 h. After cooling, water (10 mL) was added to the reaction mixture and this was then extracted with ethyl acetate. The combined organic phase was dried and concentrated in vacuo. The crude product was purified on column chromatography (EtOAc/hexane, 30:70) to give sub-title compound as a colourless syrup in 57% yield (1.26 g, 3.31 mmol).

Workup

temperatureAfter cooling
extractionthis was then extracted with ethyl acetate
customThe combined organic phase was dried
concentrationconcentrated in vacuo
customThe crude product was purified on column chromatography (EtOAc/hexane, 30:70)

Sources & evidence

ORD record: ord-4293330924ca40f5800444aa555a224b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080571B2

Reaction notes

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