Nitrogen → HCID 67518235, compound

HRID 2173278Notes

Reaction equation

HRID 2173278 reaction equation
[F:1][C:2]1[C:3](I)=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[O:7][CH2:6][CH2:5]2.N#N.[CH3:29][N:30](C=O)C>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[C-]#N.[Zn+2]>[C:29]([C:3]1[C:2]([F:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][O:7][CH:8]2[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)#[N:30]

Participants

7

Reactant 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 67515563HCID 67515563, compound

Product 1

HCID 67518235HCID 67518235, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4-[(6-fluoro-5-iodo-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate (200 mg, 0.42 mmol), Pd(PPh3)4 (200 mg) and Zn(CN)2 (300 mg, 2.6 mmol) in 20 mL of anhydrous DMF was to 110° C. at N2 atmosphere for 2 hours. The reaction was cooled to room temperature, diluted with EtOAc and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford tert-butyl 4-[(5-cyano-6-fluoro-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with prep-TLC

Sources & evidence

ORD record
ord-15cf1812d60041db8b0ee31179edb85a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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