Boron tribromide → HCID 67450195, compound

HRID 1853876Notes

Reaction equation

[CH2:1]([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]3[C:15]4[CH:28]=[CH:27][S:26][C:16]=4[C:17](=[O:25])[NH:18][C:19]=3[CH:20]=[CH:21][C:22]=2[O:23]C)=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].BrB(Br)Br>>[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14]3[C:15]4[CH:28]=[CH:27][S:26][C:16]=4[C:17](=[O:25])[NH:18][C:19]=3[CH:20]=[CH:21][C:22]=2[OH:23])=[CH:11][CH:12]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67448658HCID 67448658, compound

Product 1

HCID 67450195HCID 67450195, compoundYield 42%

Procedure

Following General Procedure F, 9-{4-[(diethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.076 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.46 mL, 0.46 mmol) to afford the desired product (12 mg, 42%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.69 (d, J=8.1 Hz, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.48-7.42 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.50 (s, 2H), 3.36-3.31 (m, 4H), 1.43 (t, J=7.3 Hz, 6H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 97.2% (AUC), tR=8.27 min.

Sources & evidence

ORD record: ord-b9afec574e4349239ac8963782fc7f9a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

Loading…