Boron tribromide → HCID 136337204, compound

HRID 1891206Notes

Reaction equation

HRID 1891206 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28]C)=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68489227HCID 68489227, compound

Product 1

HCID 136337204HCID 136337204, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of the title compound from Example 2 Step A (2.89 g, 7.06 mmol) in DCM (30 mL) was added dropwise BBr3 (21.2 mL, 1.0 M in DCM, 21.2 mmol). After addition was complete, the cooling bath was removed, and the reaction mixture was allowed to stir at room temperature. After 1.5 h, the mixture was cooled to 0° C., then was quenched by careful addition (exothermic, gas evolution) of sat aq NaHCO3 (100 mL). The resulting mixture was diluted with DCM, the phases were separated, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 35% EtOAc in hexanes, then 35 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 395.8 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 11.79 (s, 1H), 8.18 (s, 1H), 8.10 (t, J=8.0 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.49 (dd, J=10.0, 3.0 Hz, 1H), 7.09-7.06 (m, 1H), 6.98 (dd, J=9.0, 5.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. temperaturethe mixture was cooled to 0° C.
  4. customwas quenched by careful addition (exothermic, gas evolution) of sat aq NaHCO3 (100 mL)
  5. additionThe resulting mixture was diluted with DCM
  6. customthe phases were separated
  7. concentrationthe organic phase was concentrated in vacuo
  8. customPurification by chromatography on silica gel (0 to 35% EtOAc in hexanes

Sources & evidence

ORD record
ord-372f2f57d6794340a0a0f8c610b0c268
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

Loading…