HCID 135839295, compound → HCID 136115601, compound

HRID 724406Notes

Reaction equation

HRID 724406 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:18]=[C:17]2[C:13]([C:14]([C:19]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:20]=3)=[N:15][NH:16]2)=[CH:12][CH:11]=1>[Cl-].[NH+]1C=CC=CC=1>[NH:23]1[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[N:20]=[C:19]1[C:14]1[C:13]2[C:17](=[CH:18][C:10]([C:4]3[CH:5]=[CH:6][C:7]([OH:9])=[CH:8][C:3]=3[OH:2])=[CH:11][CH:12]=2)[NH:16][N:15]=1

Participants

3

Reactant 1

HCID 135839295HCID 135839295, compound

Product 1

HCID 136115601HCID 136115601, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 69401Einecs 211-027-4Solvent

Procedure

6-(2-methoxy-4-hydroxyphenyl)-3-1H-benzoimidazol-2-yl-1H-indazole, prepared in example 24(d), (46 mg, 0.13 mmol) was heated in pyridinium chloride (0.5 g) at 180° C. for 2 h. The reaction was allowed to cool, and was quenched with sat. NaHCO3 (15 mL) and extracted with EtOAc (2×20 mL). Organics were dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (60% THF/hexanes) gave 26 mg (59%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 13.49 (s, 1H), 12.94 (s, 1H), 9.49 (s, 1H), 9.39 (s, 1H), 8.43 (d, 1H, J=8.4 Hz), 7.71–7.74 (m, 2H), 7.50 (d, 1H, J=6.9 Hz), 7.43 (dd, 1H, J=8.4, 1.2 Hz), 7.16–7.23 (m, 3H), 6.45 (d, 1H, J=2.1 Hz), 6.35 (dd, 1H, J=8.4, 2.1 Hz). MS (ES) [m+H]/z calc'd 343. found 343. [m−H]/z calc'd 341. found 341.

Workup

  1. temperatureto cool
  2. customwas quenched with sat. NaHCO3 (15 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialOrganics were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (60% THF/hexanes)

Sources & evidence

ORD record
ord-433bc74afef24014becf949d09902780
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

Loading…