HCID 50994358, compound → HCID 15602889, compound

HRID 1784836Notes

Reaction equation

HRID 1784836 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[C:15]([C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH:19]=[CH:20][N:21]3[Si](C(C)C)(C(C)C)C(C)C)[CH:14]=[C:13]([C:36]([C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)=[O:37])[CH:12]=1)C1C=CC=CC=1>[OH-].[K+].CO.O.O>[NH2:10][C:11]1[CH:12]=[C:13]([C:36]([C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)=[O:37])[CH:14]=[C:15]([C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH:19]=[CH:20][NH:21]3)[CH:16]=1

Participants

5

Reactant 1

HCID 50994358HCID 50994358, compound

Product 1

HCID 15602889HCID 15602889, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14797Potassium HydroxideSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

[3-(Pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid benzyl ester (40 mg, 0.066 mmol) in 40% KOH in MeOH/H2O (5 mL/5 mL) was brought to reflux for 2 hours. After cooling down to room temperature, the mixture was diluted with water, and extracted with EtOAc. The organic layers were separated, dried and concentrated. Purification on silica gel afforded [3-amino-5-(1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone as a yellow solid (11.9 mg, 57%). 1H NMR (400 MHz, CDCl3): δ 9.01 (d, J=1.6 Hz, 1H), 8.71 (dd, J=4.8, 1.7 Hz, 1H), 8.29 (s, 1H), 8.09 (dt, J=4.9, 2.6 Hz, 1H), 7.38-7.31 (m, 3H), 7.20-7.15 (m, 4H), 7.11-7.07 (m, 2H) 6.64-6.60 (m, 1H).

Workup

  1. temperatureto reflux for 2 hours
  2. extractionextracted with EtOAc
  3. customThe organic layers were separated
  4. customdried
  5. concentrationconcentrated
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-4f5a2e78bb4c4125b24dc9e4ed5f1b33
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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