Boron tribromide → HCID 136213603, compound

HRID 332909Notes

Reaction equation

HRID 332909 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:25]=[CH:24][C:15](/[CH:16]=[CH:17]/[C:18]4[N:22]([CH3:23])[N:21]=[N:20][N:19]=4)=[CH:14][CH:13]=3)=[C:9]([C:26]3[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=3)[S:8][C:7]=2[CH:34]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:32][C:29]1[CH:28]=[CH:27][C:26]([C:9]2[S:8][C:7]3[CH:34]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]=3[C:10]=2[O:11][C:12]2[CH:25]=[CH:24][C:15](/[CH:16]=[CH:17]/[C:18]3[N:22]([CH3:23])[N:21]=[N:20][N:19]=3)=[CH:14][CH:13]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86730667HCID 86730667, compound

Product 1

HCID 136213603HCID 136213603, compoundYield 30,133,334%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 30 mL vial containing (E)-5-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)styryl)-1-methyl-1H-tetrazole (12 mg, 0.03 mmol) in DCM (1 mL) was added BBr3 (1 M in heptane, 0.077 mL, 0.08 mmol) and the reaction was stirred for 1 h at room temperature. The reaction mixture was quenched with 4 mL MeOH and stirred for 10 min at room temperature. The reaction mixture was concentrated to 50% volume and the crude product was purified by reverse phase HPLC (acidic condition, 0.1% TFA in 1-100% CH3CN/H2O) to afford (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol (4 mg, 9.04 mol, 35% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm=7.52 (d, J=16.67 Hz, 1H), 7.38-7.48 (m, 4H), 7.09 (d, J=2.02 Hz, 1H), 7.06 (d, J=8.59 Hz, 1H), 6.96 (d, J=16.67 Hz, 1H), 6.81-6.90 (m, 2H), 6.61-6.73 (m, 3H), 4.24 (s, 3H). LC/MS (m/z, MH+): 443.3.

Workup

  1. customThe reaction mixture was quenched with 4 mL MeOH
  2. stirringstirred for 10 min at room temperature
  3. concentrationThe reaction mixture was concentrated to 50% volume
  4. customthe crude product was purified by reverse phase HPLC (acidic condition, 0.1% TFA in 1-100% CH3CN/H2O)

Sources & evidence

ORD record
ord-5222b3b9b43a46c8b68254351f05f90c
Source dataset
uspto-grants-2014_11
Patent number
US08877801B2

Reaction notes

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