Boron tribromide → HCID 86689514, compound

HRID 1853839Notes

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:22]3([CH2:25][NH:26]C(=O)OC(C)(C)C)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[C:4]([O:34]C)[CH:3]=1.BrB(Br)Br>>[ClH:1].[NH2:26][CH2:25][C:22]1([C:19]2[CH:18]=[CH:17][C:16]([C:5]3[C:6]4[C:7]5[CH:15]=[CH:14][S:13][C:8]=5[C:9](=[O:12])[NH:10][C:11]=4[C:2]([Cl:1])=[CH:3][C:4]=3[OH:34])=[CH:21][CH:20]=2)[CH2:23][CH2:24]1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86689515HCID 86689515, compound

Product 1

HCID 86689514HCID 86689514, compoundYield 97.4%

Procedure

Following General Procedure F, tert-butyl (1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (50 mg, 0.09 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.58 mL, 0.58 mmol) to afford the desired product (19 mg, 48%) as a white solid: 1H NMR; (500 MHz, MeOD) δ 7.66-7.58 (m, 3H), 7.38-7.27 (m, 3H), 6.14 (d, J=5.4 Hz, 1H), 3.26 (s, 2H), 1.19 (t, J=5.5 Hz, 2H), 1.11 (t, J=5.5 Hz, 2H); ESI MS m/z 397 [C21H17ClN2O2S+H]+; HPLC 98.4% (AUC), tR=9.24 min.

Sources & evidence

ORD record: ord-2440d44cdbfc45a5824b1510316af419
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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