Boron tribromide → HCID 53472806, compound

HRID 1853871Notes

Reaction equation

[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[C:13]4[CH:26]=[CH:25][S:24][C:14]=4[C:15](=[O:23])[NH:16][C:17]=3[CH:18]=[CH:19][C:20]=2[O:21]C)=[CH:7][CH:6]=1.BrB(Br)Br>>[CH3:27][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]3[C:13]4[CH:26]=[CH:25][S:24][C:14]=4[C:15](=[O:23])[NH:16][C:17]=3[CH:18]=[CH:19][C:20]=2[OH:21])=[CH:9][CH:10]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67448089HCID 67448089, compound

Product 1

HCID 53472806HCID 53472806, compoundYield 91.5%

Procedure

Following General Procedure F, 9-{4-[2-(dimethylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (25 mg, 0.060 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.20 mL, 0.18 mmol) to afford the desired product (20 mg, 89%) as a yellow solid: 1H NMR (500 MHz, CD3CN+D2O) δ 7.55 (d, J=5.4 Hz, 1H), 7.43-7.41 (m, 3H), 7.22-7.18 (m, 3H), 5.99 (d, J=5.4 Hz, 1H), 3.00 (s, 4H), 2.56 (s, 6H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 98.3% (AUC), tR=9.24 min.

Sources & evidence

ORD record: ord-6c016951179141ccb52bfb4bcb25023f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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