Hydrochloric Acid → HCID 69590512, compound

HRID 2216403Notes

Reaction equation

HRID 2216403 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:22][CH2:23][CH2:24]Br)(=[O:21])[CH3:20].[NH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:35][CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[C:31]([CH:34]=1)[C:32]#[N:33].P(C#N)(OCC)(OCC)=O.Cl>CN(C)C=O.C(N(CC)CC)C>[C:19]([O:22][CH2:23][CH2:24][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10](=[O:12])[NH:26][C:27]1[CH:28]=[CH:29][C:30]([O:35][CH2:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[C:31]([C:32]#[N:33])[CH:34]=1)(=[O:21])[CH3:20]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 72899Indole-2-carboxylic acidHCID 76257Diethyl cyanophosphonateHCID 178227345-Amino-2-neopentyloxybenzonitrile

Product 1

HCID 69590512HCID 69590512, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

1-(Ethoxycarbonylmethyl)indole-2-carboxylic acid (2 g) obtained by reacting 1H-indol-2-carboxylic acid with potassium carbonate and bromoethyl acetate in dimethylformamide, 5-amino-2-neopentyloxybenzonitrile (1.6 g), triethylamine (2.4 g) and diethyl cyanophosphate (2 g) were added to dimethylformamide solution (20 ml) and the mixture was stirred at room temperature for 1 hr. Then the reaction mixture was treated with diluted hydrochloric acid and the organic layer was extracted with ethyl acetate. The extract solution was washed with aqueous sodium hydrogencarbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. Methanol was added to the residue to allow crystallization and the crystals were recrystallized from water-containing methanol to give the title compound (2.3 g). melting point: 169-170° C.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. washThe extract solution was washed with aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. additionMethanol was added to the residue
  6. customcrystallization
  7. customthe crystals were recrystallized from water-
  8. additioncontaining methanol

Sources & evidence

ORD record
ord-4c860c374aca4be6b1af65f346d8e2a4
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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