Phenylboronic Acid → HCID 11989686, compound

HRID 2220287Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:12][C:9]=2[C:10]=1Br)=[O:5])[CH3:2].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:12][C:9]=2[C:10]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 11989685HCID 11989685, compound

Product 1

HCID 11989686HCID 11989686, compoundYield 61%

Procedure

According to Step 6, after reaction of 3-Bromo-5-(4-tert-butylbenzene-sulfonylamino)-1-benzothiophene-2-carboxylic acid ethyl ester (469 mg, 1.0 mmol) from Example 1c) with phenylboronic acid (176 mg, 1.44 mmol) followed by chromatographic purification (silica gel, hexane/ethyl acetate (0-100% ethyl acetate) and ethyl acetate/methanol (0-15%)), the desired compound is obtained at 61% yield (300 mg).

Workup

customfollowed by chromatographic purification (silica gel, hexane/ethyl acetate (0-100% ethyl acetate) and ethyl acetate/methanol (0-15%))

Sources & evidence

ORD record: ord-e9a5377913b04965aeaa90c3c0e050f7
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417066B2

Reaction notes

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