Boron tribromide → HCID 86689522, compound

HRID 1853845Notes

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:32]=[CH:31][C:19]([CH2:20][CH2:21][N:22](C)[C:23](=O)OC(C)(C)C)=[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:32]=[CH:31][C:19]([CH2:20][CH2:21][NH:22][CH3:23])=[CH:18][CH:17]=2)=[C:4]([OH:33])[CH:3]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67449831HCID 67449831, compound

Product 1

HCID 86689522HCID 86689522, compoundYield 87%

Procedure

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (60 mg, 0.12 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.72 mL, 0.72 mmol) to afford the desired product (22 mg, 50%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.77 (s, 1H), 9.72 (s, 1H), 8.72 (s, 1H), 7.76 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.1 Hz, 2H), 7.31 (s, 1H), 7.24 (d, J=8.1 Hz, 2H), 5.85 (d, J=5.4 Hz, 1H), 3.30-3.23 (m, 2H), 3.09-3.02 (m, 2H), 2.65 (s, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=9.03 min.

Sources & evidence

ORD record: ord-0e7592c4c2784912a5057577836dd1c0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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