Boron tribromide → HCID 67450754, compound

HRID 1853834Notes

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]([CH:24]([CH3:30])[CH2:25][S:26]([NH2:29])(=[O:28])=[O:27])=[CH:20][CH:19]=1.BrB(Br)Br>>[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:19]=[CH:20][C:21]([CH:24]([CH3:30])[CH2:25][S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67449274HCID 67449274, compound

Product 1

HCID 67450754HCID 67450754, compoundYield 45.4%

Procedure

Following General Procedure F, 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide (16 mg, 0.036 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (7.0 mg, 44%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 7.68 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 2H), 7.07 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 2.57 (s, 3H), 1.86 (s, 6H); ESI MS m/z 429 [C21H20N2O4S2+H]+; HPLC 98.7%, tR=8.51 min.

Sources & evidence

ORD record: ord-848119cd6fb34e42bda5974d58223700
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

Loading…