Triethylamine → HCID 67047751, compound

HRID 606914Notes

Reaction equation

HRID 606914 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:16]=[CH:15][C:14](I)=[CH:13][C:10]=1[CH2:11][OH:12].[C:18]([C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:27]=1)[C:25]#[N:26])#[CH:19]>O1CCCC1.[Br-].[Zn+2].[Br-].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>[F:8][C:9]1[CH:16]=[CH:15][C:14]([C:19]#[C:18][C:20]2[CH:21]=[N:22][CH:23]=[C:24]([CH:27]=2)[C:25]#[N:26])=[CH:13][C:10]=1[CH2:11][OH:12]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 22220046HCID 22220046, compoundHCID 224165635-Ethynylnicotinonitrile

Product 1

HCID 67047751HCID 67047751, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve zinc (II) bromide (374 mg, 14.3 mmol) in tetrahydrofuran (30 mL) and treat with triethylamine (7.96 mL, 57.1 mmol). After 5 min add 2-fluoro -5-iodobenzyl alcohol, (prepared as described in PREPARATION 33), (3.00 g, 11.9 mmol), 5-ethynylnicotinonitrile, (prepared as described in PREPARATION 4), (1.83 g, 14.3 mmol) and tetrakis(triphenylphosphine)palladium (0) (688 mg, 0.595 mmol) to the reddish solution. Heat to 60° C. for 2 h, cool to room temperature, and filter through diatomaceous earth. Purify by silica gel chromatography, eluting with 75:25 to 60:40 hexanes:ethyl acetate, to give the title compound as a yellow crystalline solid (1.85 g, 62%).

Workup

  1. temperaturecool to room temperature
  2. filtrationfilter through diatomaceous earth
  3. customPurify by silica gel chromatography
  4. washeluting with 75:25 to 60:40 hexanes

Sources & evidence

ORD record
ord-365b126561f84a079a506e72d933722e
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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