Boron tribromide → HCID 86689478, compound

HRID 1853732Notes

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86689479HCID 86689479, compound

Product 1

HCID 86689478HCID 86689478, compoundYield 103.1%

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)ethylcarbamate (50 mg, 0.10 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 2 mL, 2 mmol) to afford the desired product (21 mg, 58%) as a light yellow solid (21 mg, 58%): 1H NMR (500 MHz, CD4OD) δ 7.65 (dt, J=5.2, 3.4 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.41 (dt, J=4.0, 2.6 Hz, 2H), 7.30 (s, 1H), 6.07 (d, J=: 5.4 Hz, 1H), 4.62 (q, J=6.8 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 371 [C19H15ClN1O2S+H]+; HPLC 97.8% (AUC), tR=9.72 min.

Sources & evidence

ORD record: ord-dd42f08ef65441ee94d8dea5a5090732
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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