Boron tribromide → HCID 86689513, compound

HRID 1853838Notes

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]([CH3:32])[CH2:23][NH:24]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[C:4]([O:33]C)[CH:3]=1.BrB(Br)Br>>[ClH:1].[NH2:24][CH2:23][C@H:22]([C:19]1[CH:18]=[CH:17][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:33])=[CH:21][CH:20]=1)[CH3:32]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67450209HCID 67450209, compound

Product 1

HCID 86689513HCID 86689513, compoundYield 83.1%

Procedure

Following General Procedure F, (S)-tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.20 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.2 mL, 1.2 mmol) to afford the desired product (35 mg, 46%) as a white solid: 1H NMR (500 MHz, MeOD) δ 7.62 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.9 Hz, 1H), 7.48 (dd, J=7.8, 1.9 Hz, 1H), 7.36 (dd, J=7.9, 1.7 Hz, 1H), 7.34-7.29 (m, 2H), 6.12 (d, J=5.4 Hz, 1H), 3.29-3.15 (m, 3H), 1.49 (d, J=6.5 Hz, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=8.74 min.

Sources & evidence

ORD record: ord-96de304d4f1942919ab720bcc5f05b10
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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