Boron tribromide → HCID 86689481, compound

HRID 1853735Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:31]=[CH:30][C:19]([CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[C:4]([O:32]C)[CH:3]=1.B(Br)(Br)Br>>[ClH:1].[NH2:22][CH2:21][CH2:20][C:19]1[CH:30]=[CH:31][C:16]([C:5]2[C:6]3[C:7]4[CH:15]=[CH:14][S:13][C:8]=4[C:9](=[O:12])[NH:10][C:11]=3[C:2]([Cl:1])=[CH:3][C:4]=2[OH:32])=[CH:17][CH:18]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67448906HCID 67448906, compound

Product 1

HCID 86689481HCID 86689481, compoundYield 23.6%

Procedure

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (79 mg, 0.25 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 9 mL, 9 mmol) to afford the desired product as a yellow solid (12 mg, 20%). 1H NMR (500 MHz, CD3OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.49 (d, J=8.1 Hz, 2H), 7.31 (d, J=7.0 Hz, 3H), 6.10 (d, J=5.4 Hz, 1H), 3.37-3.27 (m, 2H), 3.12 (t, J=7.6 Hz, 2H); ESI MS m/z 371 [C19H15ClN2O2S+H]+; HPLC 96.9% (AUC), tR=8.83 min.

Sources & evidence

ORD record: ord-86a5a99cdee14d35acaf6ff74dc23619
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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