Dimethylformamide → HCID 18009111, compound

HRID 987494Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][CH:10]=[CH2:11])=[CH:4][C:3]=1[F:13].CCOC(C)=O.[CH3:20][N:21](C=O)C>[Pd].[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>[C:20]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][CH:10]=[CH2:11])=[CH:4][C:3]=1[F:13])#[N:21]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of the crude product from Step G (39.1 mmol) and Zn(CN)2 (4.59 g, 39.1 mmol) in 50 mL of DMF was degassed by bubbling argon through the mixture for 30 minutes. Tetrakis(triphenylphosphine)palladium (3.15 g, 2.73 mmol) was added, and the reaction was heated to 80° C. The solution was stirred over the course of 7 days, twice adding additional portions (2.0 mmol) of palladium catalyst. After cooling to room temperature, the solution was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (10-15% EtOAc/hexane) provided the titled compound along with some of the aryl bromide starting material.

Workup

customby bubbling argon through the mixture for 30 minutes
temperatureAfter cooling to room temperature
washwashed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by silica gel chromatography (10-15% EtOAc/hexane)

Sources & evidence

ORD record: ord-a6aebd3617724c9587e46f37819a14af
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632818B2

Reaction notes

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