Boron tribromide → (R)-6-Chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

HRID 1853738Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]([N:24](C)[C:25](=O)OC(C)(C)C)[CH3:23])=[CH:18][CH:17]=2)=[C:4]([O:33]C)[CH:3]=1.B(Br)(Br)Br>>[ClH:1].[Cl:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]([NH:24][CH3:25])[CH3:23])=[CH:18][CH:17]=2)=[C:4]([OH:33])[CH:3]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 68229126(R)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

Product 1

HCID 67451811(R)-6-Chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one HydrochlorideYield 79.1%

Procedure

Following General Procedure F, (R)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (43 mg, 0.09 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 4 mL, 4 mmol) to afford the desired product as a white solid (15 mg, 45%): 1H NMR (500 MHz, CD3OD) δ 7.69-7.59 (m, 3H), 7.45 (ddd, J=7.0, 5.8, 2.1 Hz, 2H), 7.30 (s, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.9 Hz, 1H), 2.72 (s, 3H), 1.79 (d, J=6.9 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC 97.1% (AUC), tR=8.85 min.

Sources & evidence

ORD record: ord-d49cd48a9487418e8d7d47e99b12394b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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