Boron tribromide → HCID 25069769, compound

HRID 1035676Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]1[CH:22]=[C:23]([S:27]([NH:30][C:31]2[S:32][C:33]([CH3:36])=[N:34][N:35]=2)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]1[CH:22]=[C:23]([S:27]([NH:30][C:31]2[S:32][C:33]([CH3:36])=[N:34][N:35]=2)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 59443451HCID 59443451, compound

Product 1

HCID 25069769HCID 25069769, compoundYield 47%

Procedure

The compound is prepared by the reaction of 3-(2-methoxy-6-(3-methoxyphenyl)naphthalene-1-yl)-N-(5-methyl-1,3,4-thiadiazole-2-yl)benzenesulfonamide (0.28 mmol, 1 eq) with boron tribromide solution (2.8 ml, 2.8 mmol, 10 eq) according to method G. Purification by column chromatography with dichloromethane/methanol 95/5 as the eluent yielded the desired compound in a yield of 47%, 64 mg.

Workup

customPurification by column chromatography with dichloromethane/methanol 95/5 as the eluent

Sources & evidence

ORD record: ord-e0c6dc3d4cb9470d996c7b5a605e920a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546392B2

Reaction notes

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