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Dimethylformamide → 5-Bromo-3-isopropyl-1H-indole-7-carbonitrile

HRID 1616798
Notes
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Reaction equation

HRID 1616798 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9](I)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:12]([CH3:14])[CH3:13].[CH3:15][N:16](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:15]#[N:16])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:12]([CH3:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 678157885-bromo-7-iodo-3-(1-methylethyl)-1H-indole

Product 1

HCID 678165455-Bromo-3-isopropyl-1H-indole-7-carbonitrileYield 76%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compound
Catalyst

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 5-bromo-7-iodo-3-(1-methylethyl)-1H-indole (3.05 g, 8.38 mmol) in DMF (50 mL) was added zinc cyanide (0.52 g, 4.43 mmol) and tetrakis(triphenylphosphine)palladium (0.8 g, 0.692 mmol). The reaction was purged with N2, stirred and heated at 90° C. LCMS indicated that the reaction was complete. The reaction was evaporated to dryness under vacuum. Purification by silica gel chromatography (Analogix, SF25-60 g, 0 to 10% EtOAc in hexanes) and trituration with hexanes, filtering and drying under vacuum gave the product 5-bromo-3-(1-methylethyl)-1H-indole-7-carbonitrile (1.67 g, 6.35 mmol, 76% yield) as a light yellow solid. MS (ES)+ m/e 263.0 [M+H]+.

Workup

  1. customThe reaction was purged with N2
  2. customThe reaction was evaporated to dryness under vacuum
  3. customPurification by silica gel chromatography (Analogix
  4. filtrationSF25-60 g, 0 to 10% EtOAc in hexanes) and trituration with hexanes, filtering
  5. customdrying under vacuum

Sources & evidence

ORD record
ord-e1898d54810a49069529376f9c5d8403
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765792B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes