Dimethylformamide → HCID 58099983, compound

HRID 383340Notes

Reaction equation

HRID 383340 reaction equation
C(=O)(OC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6](Br)=[CH:5][C:4]=1[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:21][N:22](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[CH:13]1([C:4]2[C:3]([OH:2])=[CH:8][C:7]([N+:9]([O-:11])=[O:10])=[C:6]([CH:5]=2)[C:21]#[N:22])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 593949534-Bromo-2-cyclopentyl-5-nitrophenyl methyl carbonate

Product 1

HCID 58099983HCID 58099983, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
130 °C

Procedure

To a microwave vial charged with 4-bromo-2-cyclopentyl-5-nitrophenyl methyl carbonate (102 mg, 0.29 mmol), zinc cyanide (35 mg, 0.30 mmol) and Pd(PPh3)4 (21 mg, 0.02 mmol) under an N2 atmosphere was added DMF (500 μL). The reaction was heated under microwave irradiation at 130° C. for 30 min. The reaction was quenched with saturated aqueous Na2CO3 and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to yield a brown oil. Purification by silica gel chromatography (0-15% ethyl acetate/hexanes) afforded 5-cyclopentyl-4-hydroxy-2-nitrobenzonitrile as a light yellow solid (40 mg, 58% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 11.62 (s, 1H), 7.84 (s, 1H), 7.70 (s, 1H), 3.29-3.24 (m, 1H), 1.99-1.93 (m, 2H), 1.78-1.76 (m, 2H), 1.66-1.57 (m, 4H).

Workup

  1. customThe reaction was quenched with saturated aqueous Na2CO3
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a brown oil
  7. customPurification by silica gel chromatography (0-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dab845bf6ede4ad9bfa74f7893520bdf
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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