Boron tribromide → HCID 67447763, compound

HRID 1853881Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67447579HCID 67447579, compound

Product 1

HCID 67447763HCID 67447763, compoundYield 74%

Procedure

Following General Procedure F, 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (450 mg, 1.3 mmol) was reacted with tribromoborane (15 mL) to afford the desired product (320 mg, 74%) as a light brown solid: 1H NMR (500 MHz, DMSO-d6) δ 11.82 (s, 1H), 9.38 (s, 1H), 8.10 (d, J=8.3 Hz, 2H), 7.74 (d, J=5.4 Hz, 1H), 7.44-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 5.90 (d, J=5.4 Hz, 1H), 2.68 (s, 3H); ESI MS m/z 336 [C19H13NO3S+H]+; HPLC 98.3% (AUC), tR=10.59 min.

Sources & evidence

ORD record: ord-8e38aa2eb9514e3fac255d77dafdcf60
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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