Water → HCID 67109190, compound

HRID 2370995Notes

Reaction equation

HRID 2370995 reaction equation
[H-].[Na+].[Br:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.O(C1C=CC(C(C2C=CC(OC#N)=CC=2)(C)C)=CC=1)[C:22]#[N:23].O>C1COCC1.[Cl-].[Na+].O>[Br:3][C:4]1[N:5]([C:22]#[N:23])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 708721,3-Bis(4-cyanophenyl)propaneHCID 67109249HCID 67109249, compound

Product 1

HCID 67109190HCID 67109190, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

NaH (18.35 mg, 0.76 mmol) was stirred in dry THF (1 ml) at 0° C. and 2-bromo-3-(4-methoxyphenyl)-1H-indole (210 mg, 0.69 mmol) dissolved in dry THF (4.5 ml) was added dropwise. The mixture was stirred at 0° C. for 5 min and then 2,2-bis-(4-cyanatophenyl)propane (251 mg, 0.90 mmol) dissolved in dry THF (4.5 ml) was added dropwise. Water was added and this mixture was stirred for 30 min Brine was added and the aqueous mixture was extracted with DCM. The solvent was concentrated and the crude product was purified on silica (EtOAc/n-Heptane 1:4). 198 mg 2-bromo-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile was obtained.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. additionwas added
  4. extractionthe aqueous mixture was extracted with DCM
  5. concentrationThe solvent was concentrated
  6. customthe crude product was purified on silica (EtOAc/n-Heptane 1:4)

Sources & evidence

ORD record
ord-b3620576353e4d5fa0ced287d5659091
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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