Boron tribromide → HCID 67450338, compound

HRID 1853740Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[NH:9][C:8](=[O:14])[C:7]3[S:15][CH:16]=[CH:17][C:6]=3[C:5]=2[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([CH3:35])[CH2:25][N:26](C)[C:27](=O)OC(C)(C)C)=[CH:20][CH:19]=1.B(Br)(Br)[Br:37]>>[BrH:37].[OH:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[NH:9][C:8](=[O:14])[C:7]3[S:15][CH:16]=[CH:17][C:6]=3[C:5]=2[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([CH3:35])[CH2:25][NH:26][CH3:27])=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67449017(R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Product 1

HCID 67450338HCID 67450338, compoundYield 65%

Procedure

Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (2.08 g, 4.23 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 40 mL, 40 mmol) to afford the desired product as a yellow solid (1.05 g, 65%); 1H NMR (500 MHz, CD3OD) δ 7.60-7.54 (m, 2H), 7.46 (dd, J=7.8, 1.9 Hz, 1H), 7.37 (dd, J=7.9, 1.8 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (d, J=0.8 Hz, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.37-3.24 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.74 min.

Sources & evidence

ORD record: ord-b6f53e3e771a4fa3b12c2a83862409fe
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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