Boron tribromide → (E)-2-(4-fluoro-2-methylphenyl)-3-(4-(2-(5-methyl-4H-1,2,4-triazol-3-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol

HRID 332908Notes

Reaction equation

HRID 332908 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17]C)[CH:15]=[CH:16][C:10]=3[C:9]=2[O:19][C:20]2[CH:33]=[CH:32][C:23](/[CH:24]=[CH:25]/[C:26]3[NH:30][C:29]([CH3:31])=[N:28][N:27]=3)=[CH:22][CH:21]=2)=[C:4]([CH3:34])[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:10]=3[C:9]=2[O:19][C:20]2[CH:21]=[CH:22][C:23](/[CH:24]=[CH:25]/[C:26]3[NH:30][C:29]([CH3:31])=[N:28][N:27]=3)=[CH:32][CH:33]=2)=[C:4]([CH3:34])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178487663HCID 178487663, compound

Product 1

HCID 178434028(E)-2-(4-fluoro-2-methylphenyl)-3-(4-(2-(5-methyl-4H-1,2,4-triazol-3-yl)vinyl)phenoxy)benzo[b]thiophen-6-olYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 30 mL screw cap vial, (E)-3-(4-((2-(4-fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)styryl)-5-methyl-4H-1,2,4-triazole (15 mg, 0.032 mmol) was dissolved in DCM (1 mL). The vial was charged with BBr3 (1.0 M in hexanes, 0.095 ml, 0.095 mmol) and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was quenched with 4 mL MeOH and stirred for 10 min. The mixture was concentrated to 50% volume and purified by reverse phase HPLC (acidic condition, 0.1% TFA in 30-100% CH3CN/H2O) to afford (E)-2-(4-fluoro-2-methylphenyl)-3-(4-(2-(5-methyl-4H-1,2,4-triazol-3-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol (7 mg, 0.015 mmol, 48% yield) as a pale yellow solid. 1H NMR (400 MHz, CD3OD) δ ppm=2.26 (s, 3H), 2.42 (s, 3H), 6.72-6.83 (m, 5H), 6.88 (dd, J=10.11, 2.53 Hz, 1H), 7.14 (d, J=2.02 Hz, 1H), 7.16-7.26 (m, 2H), 7.29-7.41 (m, 3H). LC/MS (m/z, MH+): 458.1.

Workup

  1. customTo a 30 mL screw cap vial
  2. customThe reaction mixture was quenched with 4 mL MeOH
  3. stirringstirred for 10 min
  4. concentrationThe mixture was concentrated to 50% volume
  5. custompurified by reverse phase HPLC (acidic condition, 0.1% TFA in 30-100% CH3CN/H2O)

Sources & evidence

ORD record
ord-f44557f0759940d78736c3dfa243db76
Source dataset
uspto-grants-2014_11
Patent number
US08877801B2

Reaction notes

Loading…