Dimethylformamide → 4-(4-Fluoro-1H-pyrrolo[2,3-b]pyridin-5-yloxy)-5-methyl-pyrrolo[2,1-f][1,2,4]triazin-6-ol

HRID 1064233Notes

Reaction equation

HRID 1064233 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[CH:12]([O-:14])=O.[NH4+:15].C[N:17]([CH:19]=O)[CH3:18]>[Pd]>[F:1][C:2]1[C:7]([O:8][C:18]2[C:4]3=[C:3]([CH3:2])[C:12]([OH:14])=[CH:6][N:5]3[N:15]=[CH:19][N:17]=2)=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2723923Ammonium formateHCID 222736554-Fluoro-1H-pyrrolo[2,3-B]pyridin-5-OL

Product 1

HCID 98177604-(4-Fluoro-1H-pyrrolo[2,3-b]pyridin-5-yloxy)-5-methyl-pyrrolo[2,1-f][1,2,4]triazin-6-olYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of Example 4 (84 mg, 0.22 mmol) in DMF (1.1 mL), 10% Pd on charcoal (10 mg) and ammonium formate (68 mg, 1.08 mmol) were added. The mixture was stirred at RT for 20 h then filtered through Celite® and concentrated in vacuo. The resulting solid was dissolved in methanol and purified by SCX-silica column (18 g) by washing with methanol (2×8 mL) and then by eluting a solution of 2M ammonia in methanol (2×8 mL) to give the title compound (60 mg, 93%) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 12.16 (1H, s), 9.53 (1H, s), 8.29 (1H, d, J=9.6 Hz), 7.88 (1H, s), 7.61 (1H, t, J=3.0 Hz), 7.55 (1H, s), 6.59 (1H, dd, J=2.0, 3.5 Hz), 2.40 (3H, s). LC/MS=m/z 300 (M+H)+.

Workup

  1. filtrationthen filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting solid was dissolved in methanol
  4. custompurified by SCX-silica column (18 g)
  5. washby washing with methanol (2×8 mL)
  6. washby eluting a solution of 2M ammonia in methanol (2×8 mL)

Sources & evidence

ORD record
ord-b20e037489bc419ab611261a312b3102
Source dataset
uspto-grants-2005_11
Patent number
US06969717B2

Reaction notes

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