Methanol → HCID 44465845, compound

HRID 383449Notes

Reaction equation

HRID 383449 reaction equation
[CH:1]([C:4]1[N:5]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[C:6]2[C:11]([C:12]=1[C:13]#[N:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]([C:13]#[N:14])=[C:4]2[CH:1]([CH3:3])[CH3:2])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 66898503HCID 66898503, compound

Product 1

HCID 44465845HCID 44465845, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Isopropyl-1-(4-methoxy-phenyl)-1H-indole-3-carbonitrile (3 mg, 0.01 mmol) was dissolved in dry CH2Cl2 (0.5 ml) and stirred at 0° C. BBr3 (1M in CH2Cl2, 50 μl) was added and the mixture left in the fridge with stirring overnight. Some drops of MeOH were added and stirred. The solvent was removed in vacuo and the mixture partitioned in H2O/DCM. The organic phase was separated using a phase separator. The solvent was removed in vacuo and the mixture was chromatographed using a prepacked silica column (solvent: EtOAc:n-Heptane 3-7) to afford the desired 1-(4-hydroxy-phenyl)-2-isopropyl-1H-indole-3-carbonitrile (1.1 mg, 39%). 1H NMR (acetone-d6, 500 MHz): 7.64 (m, 1H), 7.32 (m, 2H), 7.28 (m, 1H), 7.22 (m, 1H), 7.11 (m, 2H), 6.98 (m, 1H), 3.07 (m, 1H) and 1.43 (d, 6H, J=7.0 Hz).

Workup

  1. waitthe mixture left in the fridge
  2. stirringwith stirring overnight
  3. stirringstirred
  4. customThe solvent was removed in vacuo
  5. customthe mixture partitioned in H2O/DCM
  6. customThe organic phase was separated
  7. customThe solvent was removed in vacuo
  8. customthe mixture was chromatographed

Sources & evidence

ORD record
ord-cc5f706e564f41238d20bd607050296a
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

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