Methanol → HCID 21081506, compound

HRID 2117150Notes

Reaction equation

HRID 2117150 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-8099d5c0d4574e3caeca0fc3868a1cc4
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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