Methanol → HCID 21081730, compound

HRID 347579Notes

Reaction equation

HRID 347579 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][CH:12]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:6]=12.CO.C1COCC1.[Cl-].[NH4+]>CCOC(C)=O.[Zn]>[NH2:22][C:20]1[CH:19]=[CH:18][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[NH:11][CH:12]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:6]=23)=[C:2]([F:1])[CH:21]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21081729Methyl 4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 21081730HCID 21081730, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (230 mg, 0.69 mmol) in a mixed solvent (10 mL of MeOH and 10 mL of THF) were added ammonium chloride (185 mg, 3.45 mmol) and zinc dust (226 mg, 3.45 mmol). The reaction mixture was stirred at room temperature overnight, diluted with EtOAc (50 ml), and filtered through a pad of Celite®. The filtrate was concentrated in vacuo to give the desired product (207 mg, 100%) as a yellow solid. MS(ESI+) m/z 302.2 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-431a9dd100574b758adc1edd2135016e
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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