Dimethylformamide → HCID 18446947, compound

HRID 1268931Notes

Reaction equation

HRID 1268931 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][C@H:10]([CH2:12][CH3:13])[CH3:11])=[C:4]([F:14])[CH:3]=1.[CH3:15][N:16](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:14][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([F:8])[C:5]=1[O:9][C@H:10]([CH2:12][CH3:13])[CH3:11])[C:15]#[N:16]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 18446944HCID 18446944, compound

Product 1

HCID 18446947HCID 18446947, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 400 mg (1.5 mmol) of 1-bromo-3,5-difluoro-4-(2-(S)-butoxy)benzene (from Step A), 106 mg (0.9 mmol) of zinc cyanide, 69 mg of tris(dibenzylideneacetone)dipalladium(0) and 100 mg (0.18 mmol) of 1,1′-bis(diphenylphosino)ferrocene in 3 mL of DMF and 30 μL of water. The resulting solution was heated to 80° C. for 1 h and then cooled and concentrated. Chromatography on a Biotage 40M cartridge using 20:1 v/v hexanes/EtOAc as the eluant afforded 280 mg of the title compound: 1H NMR (500 Mhz) δ 1.01 (t, J=7.6, 3H), 1.35 (d, J=6.2, 3H), 1.68 (m, 1H), 1.79 (m, 1H), 4.47 (m, 1H), 7.25 (d, 2H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e017fee1307a40a68af1f6ae34521440
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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