Boron tribromide → HCID 68229183, compound

HRID 1853819Notes

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]([NH:26]C(=O)OC(C)(C)C)[CH3:25])=[CH:20][CH:19]=1.BrB(Br)Br>>[NH2:26][C@@H:24]([C:21]1[CH:20]=[CH:19][C:18]([C:4]2[C:5]3[C:6]4[CH:17]=[CH:16][S:15][C:7]=4[C:8](=[O:14])[NH:9][C:10]=3[C:11]([CH3:13])=[CH:12][C:3]=2[OH:2])=[CH:23][CH:22]=1)[CH3:25]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86689506HCID 86689506, compound

Product 1

HCID 68229183HCID 68229183, compoundYield 54.1%

Procedure

Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (43 mg, 0.095 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 51%) as a grey solid: 1H NMR (300 MHz, DMSO-d6) δ 10.72 (s, 1H), 8.52 (s, 3H), 7.65 (dd, J=13.3, 6.8 Hz, 3H), 7.30 (d, J=8.2 Hz, 2H), 7.06 (s, 1H), 5.87 (d, J=5.4 Hz, 1H), 4.64-4.45 (m, 1H), 2.50 (s, 3H), 1.63 (d, J=6.8 Hz, 3H); ESI MS m/z 480 [C27H33N3O3S+H]+; HPLC 98.6%, tR=8.42 min.

Sources & evidence

ORD record: ord-e629a932c0a54072b7e6e68f405d4127
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

Loading…