Methanol → HCID 21081506, compound

HRID 347546Notes

Reaction equation

HRID 347546 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=2[F:25])[NH:8][CH:7]=1)=[O:5].C1COCC1.CO.[Cl-].[NH4+]>CCOC(C)=O.[Zn]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:13]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:8][CH:7]=[C:6]([C:4](=[O:5])[CH2:3][N:2]([CH3:26])[CH3:1])[C:14]=23)=[C:17]([F:25])[CH:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21081572HCID 21081572, compound

Product 1

HCID 21081506HCID 21081506, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(dimethylamino)-1-(4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone (80 mg, 0.22 mmol) in a mixed solvent (5 mL of THF and 5 mL of MeOH) were added ammonium chloride (64.2 mg, 1.2 mmol, EMD) and Zn dust (78.4 mg, 1.2 mmol, Aldrich). The reaction mixture was stirred at room temperature overnight, diluted with 30 mL of EtOAc and filtered through a pad of Celite®. The filtrate was concentrated in vacuo and the resulting residue was purified by preparative HPLC. The desired fractions were combined, neutralized with saturated aq. NaHCO3 solution, and concentrated in vacuo. The solid that formed was collected by filtration (51 mg, 71%). MS(ESI+) m/z 328.1 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by preparative HPLC
  4. concentrationconcentrated in vacuo
  5. customThe solid that formed
  6. filtrationwas collected by filtration (51 mg, 71%)

Sources & evidence

ORD record
ord-71445263a7634ce981c784d7689481ae
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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