Boron tribromide → HCID 86689524, compound

HRID 1853847Notes

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:21]=[CH:20][C:19]([C@@H:22]([N:24](C)[C:25](=O)OC(C)(C)C)[CH3:23])=[CH:18][CH:17]=2)=[C:4]([O:33]C)[CH:3]=1.BrB(Br)Br>>[ClH:1].[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:21]=[CH:20][C:19]([C@@H:22]([NH:24][CH3:25])[CH3:23])=[CH:18][CH:17]=2)=[C:4]([OH:33])[CH:3]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86689526HCID 86689526, compound

Product 1

HCID 86689524HCID 86689524, compoundYield 106.8%

Procedure

Following General Procedure F, (S)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (40 mg, 0.08 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.48 mL, 0.48 mmol) to afford the desired product (18 mg, 60%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.72-7.60 (m, 3H), 7.49-7.39 (m, 2H), 7.30 (s, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.49 (q, J=6.9 Hz, 1H), 2.73 (d, J=4.3 Hz, 3H), 1.80 (d, J=6.9 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=13.60 min.

Sources & evidence

ORD record: ord-52cc4a7da7c849b6b095d87fab06ebdf
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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