Boron tribromide → 9-[4-(Aminomethyl)phenyl]-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one

HRID 1853889Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][C:15]([CH3:17])=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:18]1[CH:32]=[CH:31][C:21]([CH2:22][NH:23]C(=O)OC(C)(C)C)=[CH:20][CH:19]=1.BrB(Br)Br>>[NH2:23][CH2:22][C:21]1[CH:31]=[CH:32][C:18]([C:4]2[C:5]3[C:6]4[CH:16]=[C:15]([CH3:17])[S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[OH:2])=[CH:19][CH:20]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 68229071tert-Butyl 4-(8-Methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Product 1

HCID 534728089-[4-(Aminomethyl)phenyl]-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-oneYield 37%

Procedure

Following General Procedure F, tert-butyl 4-(8-methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (80 mg, 0.17 mmol) was reacted with tribromoborane (2.0 mL) to afford the desired product (20 mg, 37%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=8.9 Hz, 2H), 7.40-7.37 (m, 3H), 7.15 (d, J=8.1 Hz, 1H), 5.76 (s, 1H), 4.28 (s, 2H), 2.33 (s, 3H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC >99%, tR=5.91 min.

Sources & evidence

ORD record: ord-ce4fb613ca0b4d0a99e7f70f5e4a81d4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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