Ammonium Chloride → HCID 21081657, compound

HRID 347554Notes

Reaction equation

HRID 347554 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][C:4]#[C:5][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])[N:8](C(OC(C)(C)C)=O)[CH:7]=1.[NH4+].[Cl-]>C1COCC1.CO.CCOC(C)=O.[Zn]>[CH3:33][N:2]([CH3:1])[CH2:3][C:4]#[C:5][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]([NH2:22])=[CH:18][C:17]=2[F:25])[NH:8][CH:7]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 21081808HCID 21081808, compound

Product 1

HCID 21081657HCID 21081657, compoundYield 90.7%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl 3-(3-(dimethylamino)prop-1-ynyl)-4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (170 mg, 0.374 mmol) in THF (10 mL) and MeOH (10 mL), was added Zn powder (<10 micron, 500 mg) and NH4Cl (500 mg). The reaction mixture was stirred at rt for 2 h, diluted with EtOAc, and filtered through a pad of Celite®. The filtrate was washed with sat. aq. KH2PO4 solution, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product (110 mg, 90%) as a yellow solid. LC/MS(ESI+) m/z 325 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. washThe filtrate was washed with sat. aq. KH2PO4 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bac0b7ac485743d0bcb094a2abaf9219
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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