Boron tribromide → 9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

HRID 1853842Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[C:16]([C:18]2[C:19]3[C:20]4[CH:34]=[CH:33][S:32][C:21]=4[C:22](=[O:31])[NH:23][C:24]=3[C:25]([Cl:30])=[CH:26][C:27]=2[O:28]C)[CH:15]=[CH:14][C:3]=1[CH2:4][CH2:5][NH:6]C(=O)OC(C)(C)C.BrB(Br)Br>>[ClH:1].[NH2:6][CH2:5][CH2:4][C:3]1[CH:14]=[CH:15][C:16]([C:18]2[C:19]3[C:20]4[CH:34]=[CH:33][S:32][C:21]=4[C:22](=[O:31])[NH:23][C:24]=3[C:25]([Cl:30])=[CH:26][C:27]=2[OH:28])=[CH:17][C:2]=1[Cl:1]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67450246Tert-butyl 2-chloro-4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Product 1

HCID 866895189-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one HydrochlorideYield 108.8%

Procedure

Following General Procedure F, tert-butyl 2-chloro-4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (80 mg, 0.154 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.92 mL, 0.92 mmol) to afford the desired product (37 mg, 59%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.68 (d, J=5.4 Hz, 1H), 7.56 (d, J=7.8 Hz, 1H), 7.42 (d, J=1.7 Hz, 1H), 7.30 (s, 1H), 7.27 (dd, J=7.8, 1.7 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.39-3.25 (m, 4H); ESI MS m/z 405 [C19H14Cl2N2O2S+H]+; HPLC 98.1% (AUC), tR=9.17 min.

Sources & evidence

ORD record: ord-24c595a7313649c6afafb3880d10b860
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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