Imidazole → HCID 57330084, compound

HRID 1054120Notes

Reaction equation

HRID 1054120 reaction equation
Br[CH2:2][C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][N:4]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:15]1([CH2:2][C:3]2[CH:8]=[N:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:5][N:4]=2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 67511398HCID 67511398, compound

Product 1

HCID 57330084HCID 57330084, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Synthesized using compound 71a (100 mg, 0.40 mmol), imidazole (109 mg, 1.60 mmol) and K2CO3 (276 mg, 2.00 mmol) in DMF according to Method B. Crude product was purified by flash chromatography on silica-gel using ethyl acetate as eluent. Light yellow solid. Yield: 69 mg, 73%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=5.50 (s, 2H), 7.24 (t, J=1.3 Hz, 1H), 7.33 (t, J=1.1 Hz, 1H), 7.64-7.74 (m, 3H), 7.86 (s, 1H), 8.17-8.23 (m, 2H), 8.63 (d, J=1.3 Hz, 1H), 9.18 (d, J=1.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=50.0, 119.2, 126.9, 129.1, 130.2, 130.3, 135.7, 137.5, 141.5, 142.3, 152.3; (ESI): m/z=236.91 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel

Sources & evidence

ORD record
ord-13874d2d7e8a4347afd8e2d84e90046e
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…