Boron tribromide → HCID 86689545, compound

HRID 1853864Notes

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:30]=[CH:29][C:19]([CH2:20][NH:21]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[C:4]([O:31]C)[CH:3]=1.BrB(Br)Br>>[ClH:1].[NH2:21][CH2:20][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:31])=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86689499HCID 86689499, compound

Product 1

HCID 86689545HCID 86689545, compoundYield 158.9%

Procedure

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (15 mg, 0.032 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1 mL, 1 mmol) to afford the desired product (10 mg, 80%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 7.64 (d, J=8.2 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.43-7.38 (m, 2H), 7.30 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.27 (s, 2H); ESI MS m/z 357 [C18H13ClN2O2S+H]+; ESI MS m/z 357 [C18H13ClN2O2S+H]+; HPLC 98.4% (AUC), tR=8.62 min.

Sources & evidence

ORD record: ord-ebd3d235fda749ecaf1bcae39cf70e68
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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