HCID 67447393, compound → HCID 67447134, compound

HRID 1853887Notes

Reaction equation

HRID 1853887 reaction equation
[NH2:1][CH2:2][CH2:3][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>BrB(Br)Br>[NH2:1][CH2:2][CH2:3][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

Participants

3

Reactant 1

HCID 67447393HCID 67447393, compound

Product 1

HCID 67447134HCID 67447134, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

Following General Procedure F, 9-[4-(2-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 1.8 mmol) was reacted with tribromoborane (10 mL) to afford the desired product (520 mg, 88%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.78 (s, 1H), 9.20 (s, 1H), 7.88 (br s, 2H), 7.69 (d, J=5.4 Hz, 1H), 7.41-7.36 (m, 3H), 7.22 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.88 (d, J=5.4 Hz, 1H), 3.21-3.14 (m, 2H), 3.01-2.98 (m, 2H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC >99% (AUC), tR=7.72 min.

Sources & evidence

ORD record
ord-59d51049290f4973b9fc3c076aa714a0
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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