Boron tribromide → HCID 66939497, compound

HRID 1255197Notes

Reaction equation

HRID 1255197 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]([N:14]2[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]2)[S:12][CH:13]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]([N:14]2[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]2)[S:12][CH:13]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66939344HCID 66939344, compound

Product 1

HCID 66939497HCID 66939497, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of the title compound from Example 17 Step A (353 mg, 0.888 mmol) in DCM (6.3 ml) was added BBr3 (2.67 ml, 1.0 M in DCM, 2.67 mmol) dropwise. After the addition was complete, the mixture was allowed to warm up to ambient temperature. After 1 h, the reaction mixture was quenched by addition of sat. aq. NaHCO3 and extracted with DCM. The organic phase was separated and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 60% EtOAc in hexanes) provided the title compound as a yellow solid: LCMS m/z 384.5 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 10.17 (s, 1H), 8.18 (s, 1H), 7.67 (dd, J=8.0, 1.9 Hz, 1H), 7.34 (t, J=8.5 Hz, 1H), 7.09 (dd, J=8.2, 0.9 Hz, 1H), 6.98 (t, J=7.4 Hz, 1H), 4.45 (m, 2H), 1.44 (t, J=7.1 Hz, 3H).

Workup

  1. additionAfter the addition
  2. customthe reaction mixture was quenched by addition of sat. aq. NaHCO3
  3. extractionextracted with DCM
  4. customThe organic phase was separated
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5e961ab15c534aebbe76a2f31a5128eb
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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