Boron tribromide → 9-(4-(1-Aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride
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]([CH:22]([CH2:32][CH3:33])[CH2:23][NH:24]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[C:4]([O:34]C)[CH:3]=1.BrB(Br)Br>>[ClH:1].[NH2:24][CH2:23][CH:22]([C:19]1[CH:18]=[CH:17][C:16]([C:5]2[C:6]3[C:7]4[CH:15]=[CH:14][S:13][C:8]=4[C:9](=[O:12])[NH:10][C:11]=3[C:2]([Cl:1])=[CH:3][C:4]=2[OH:34])=[CH:21][CH:20]=1)[CH2:32][CH3:33]Participants
3
Procedure
Following General Procedure F, tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (65 mg, 0.13 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.76 mL, 0.76 mmol) to afford the desired product (28 mg, 56%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.60 (d, J=5.4 Hz, 1H), 7.54 (dd, J=7.9, 1.8 Hz, 1H), 7.44 (dd, J=7.7, 1.8 Hz, 1H), 7.39 (dd, J=7.9, 1.8 Hz, 1H), 7.35-7.30 (m, 2H), 6.08 (d, J=5.4 Hz, 1H), 3.38-3.22 (m, 2H), 2.98-2.89 (m, 1H), 1.97-1.85 (m, 1H), 1.85-1.72 (m, 1H), 0.98 (t, J=7.4 Hz, 3H); ESI MS m/z 399 [C21H19ClN2O2S+H]+; HPLC >99%, (AUC), tR=10.29 min.
Sources & evidence
- ORD record
- ord-a21903f0ae304fb0b661d2e5734911dc
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962648B2
Reaction notes
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