Boron tribromide → HCID 58338542, compound

HRID 445213Notes

Reaction equation

B(Br)(Br)Br.Cl.C[O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)=[C:13]([C:34]1[C:35]([C:39]#[N:40])=[CH:36][S:37][CH:38]=1)[CH:12]=[CH:11]2>ClCCl>[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([O:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:23][CH:24]=1)=[C:13]([C:34]1[C:35]([C:39]#[N:40])=[CH:36][S:37][CH:38]=1)[CH:12]=[CH:11]2

Participants

Conditions

Temperature: 0 °C

Procedure

Slowly add boron tribromide in dichloromethane (4 M, 182 μL, 728.0 μmol) to a solution of 4-(6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl)thiophene-3-carbonitrile hydrochloride (95 mg, 182.3 μmol) and dichloromethane (4 mL) stirring at 0° C. Stir the mixture at 0° C. for 1.5 hours. Quench the mixture with aqueous sodium bicarbonate. Extract the mixture 3 times with 20% methanol/dichloromethane. Wash the combined organic layers with water. Dry the resulting solution over sodium sulfate, filter, and concentrate to dryness. Purify the residue by flash chromatography on silica to obtain the title compound (52 mg, 111.2 μmol).

Workup

customQuench the mixture with aqueous sodium bicarbonate
extractionExtract the mixture 3 times with 20% methanol/dichloromethane
washWash the combined organic layers with water
dry with materialDry the resulting solution over sodium sulfate
filtrationfilter
concentrationconcentrate to dryness
customPurify the residue by flash chromatography on silica

Sources & evidence

ORD record: ord-44e3449683d342189304392efa0a77aa
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476300B2

Reaction notes

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