Boron tribromide → HCID 86689516, compound

HRID 1853840Notes

Reaction equation

[ClH:1].[NH2:2][CH2:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:14]4[C:15]5[CH:29]=[CH:28][S:27][C:16]=5[C:17](=[O:26])[NH:18][C:19]=4[C:20]([Br:25])=[CH:21][C:22]=3[O:23]C)=[CH:9][CH:8]=2)[CH2:6][CH2:5]1.BrB(Br)Br>>[ClH:1].[NH2:2][CH2:3][C:4]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[C:14]4[C:15]5[CH:29]=[CH:28][S:27][C:16]=5[C:17](=[O:26])[NH:18][C:19]=4[C:20]([Br:25])=[CH:21][C:22]=3[OH:23])=[CH:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67450013HCID 67450013, compound

Product 1

HCID 86689516HCID 86689516, compoundYield 54%

Procedure

Following General Procedure F, 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (100 mg, 0.22 mmol was reacted with tribromoborane (1.0 M in methylene chloride, 1.32 mL, 1.32 mmol) to afford the desired product (52 mg, 54%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.63 (t, J=6.8 Hz, 3H), 7.48 (s, 1H), 7.33 (d, J=8.2 Hz, 2H), 6.14 (d, J=5.4 Hz, 1H), 3.26 (s, 2H), 1.19 (t, J=5.6 Hz, 2H), 1.12 (t, J=5.5 Hz, 2H); ESI MS m/z 442 [C21H17BrN2O2S+H]+; HPLC >99% (AUC), tR=9.25 min.

Sources & evidence

ORD record: ord-b58cb46b9daa467991ff75384915db45
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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