Dimethylformamide → HCID 86623738, compound

HRID 1173472Notes

Reaction equation

HRID 1173472 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:9][CH2:10][OH:11])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[NH4+].[OH-].[CH3:23][N:24](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[OH:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:5]1[CH:6]=[CH:7][C:2]([C:23]#[N:24])=[CH:3][C:4]=1[C:17]([F:20])([F:19])[F:18]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 59557180HCID 59557180, compound

Product 1

HCID 86623738HCID 86623738, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[[4-bromo-2-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethanol (0.699 g, 1.92 mmol) and Zn(CN)2 (0.157 g, 1.34 mmol) in DMF (5 mL) was sparged with N2 for 15 min at rt and Pd(PPh3)4 (0.111 g, 0.096 mmol) was added in one portion, taking care not to allow air into the reaction flask. The mixture was heated to 80° C. under N2 for 40 min, cooled, poured into dilute NH4OH, and the whole was extracted with Et2O (×3). The combined organic portions were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.571 g of the title compound as a colorless gum: 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=1.6 Hz, 1H), 7.82 (dd, J=8.4, 1.8 Hz, 1H), 7.56 (d, J=8.6 Hz, 1H), 3.86 (q, J=8.9 Hz, 2H), 3.69 (t, J=2H), 3.50 (t, J=5.2 Hz, 2H), 1.74 (bs, 1H).

Workup

  1. customwas sparged with N2 for 15 min at rt
  2. temperaturecooled
  3. extractionthe whole was extracted with Et2O (×3)
  4. washThe combined organic portions were washed (water, brine)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-d235162abdf843c2b238924e170e4826
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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