Triethylamine → HCID 67047551, compound

HRID 606910Notes

Reaction equation

HRID 606910 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:16]=1)[C:14]#[N:15].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:35][C:36]1[CH:46]=[CH:45][C:44]([C:47]#[C:48][Si](C)(C)C)=[CH:43][C:37]=1[CH2:38][NH:39][C:40](=[O:42])[CH3:41]>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>[C:14]([C:13]1[CH:16]=[C:9]([C:48]#[C:47][C:44]2[CH:45]=[CH:46][C:36]([F:35])=[C:37]([CH:43]=2)[CH2:38][NH:39][C:40](=[O:42])[CH3:41])[CH:10]=[N:11][CH:12]=1)#[N:15]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 7367935-BromonicotinonitrileHCID 2724141Tetrabutylammonium FluorideHCID 67047813N-(2-Fluoro-5-trimethylsilanylethynylbenzyl)-acetamide

Product 1

HCID 67047551HCID 67047551, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Add zinc (II) bromide (313 mg, 1.20 mmol), triethylamine (0.67 mL, 4.80 mmol), 5-bromonicotinonitrile (183 mg, 1.00 mmol), tetrakis(triphenylphosphine)palladium (0) (58 mg, 0.050 mmol), and a 1.0 M solution of tetrabutylammonium fluoride (2.0 mL) in tetrahydrofuran to a solution of N-(2-fluoro-5-trimethylsilanylethynylbenzyl) -acetamide, (prepared as described in PREPARATION 31), (289 mg, 1.10 mmol) in anhydrous tetrahydrofuran (2.5 mL) under nitrogen. Heat to 60° C. for 5 h, cool to room temperature, and filter through diatomaceous earth. Concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 50:50 hexanes:ethyl acetate, to give the title compound as a white crystalline solid (122 mg, 42%).

Workup

  1. temperaturecool to room temperature
  2. filtrationfilter through diatomaceous earth
  3. concentrationConcentrate
  4. custompurify the residue by silica gel chromatography
  5. washeluting with 100:0 to 50:50 hexanes

Sources & evidence

ORD record
ord-7525c7349dca44418aaed54e85516603
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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