4-Iodoaniline → HCID 59425315, compound

HRID 502228Notes

Reaction equation

HRID 502228 reaction equation
[Li+].[CH3:2][CH:3]([N-:5][CH:6]([CH3:8])[CH3:7])[CH3:4].I[C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.[C:17]([O-:20])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C>[NH2:14][C:13]1[CH:15]=[CH:16][C:10]([C:11]2[N:5]([CH:6]3[CH2:8][CH2:7]3)[C:3]3[C:4]([C:12]=2[C:13]#[N:14])=[CH:10][CH:16]=[C:15]([O:20][CH3:17])[CH:2]=3)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 2724682Lithium diisopropylamide

Product 1

HCID 59425315HCID 59425315, compoundYield 124.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the intermediate (2.65 g, 12.5 mmol) obtained above and triisopropyl borate (3.38 g, 4.14 mL, 18.8 mmol) in dry THF (18 mL) at −78° C. is added LDA (10 mL, 1.5 M, 15.0 mmol). The mixture is stirred at −78° C. for 15 min after the addition, then slowly brought to room temperature and stirred for 30 min. It is then cooled at −78° C. and followed by the addition of 4-iodoaniline (3.29 g, 15.0 mmol), PdCl2(dppf) (0.46 g, 0.6 mmol), DMF (40 mL) and K2CO3 (18.8 mL, 2.0 M, 37.6 mmol). The mixture is brought to room temperature slowly and stirred overnight and then poured into ice-water (400 mL). The precipitate is collected and washed with water, and after drying, is chromatographed (silica gel, EtOAc/DCM, 0.5/9.5) to furnish 2-(4-aminophenyl)-1-cyclopropyl-6-methoxyindole-3-carbonitrile (2.84 g, 75%).

Workup

  1. additionafter the addition
  2. customslowly brought to room temperature
  3. stirringstirred for 30 min
  4. temperatureIt is then cooled at −78° C.
  5. customis brought to room temperature
  6. stirringstirred overnight
  7. customThe precipitate is collected
  8. washwashed with water
  9. customafter drying
  10. customis chromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

Sources & evidence

ORD record
ord-6d100d1d044d415f92099771f8af2645
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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