HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → 2-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-N-methylbenzamide

HRID 606940
Notes
Print preview

Reaction equation

HRID 606940 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)#[CH:2].[F:11][C:12]1[CH:21]=[CH:20][C:19](I)=[CH:18][C:13]=1[C:14]([NH:16][CH3:17])=[O:15].C(N(CC)CC)C>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:11][C:12]1[CH:21]=[CH:20][C:19]([C:2]#[C:1][C:3]2[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=2)=[CH:18][C:13]=1[C:14]([NH:16][CH3:17])=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 210973493-Ethynyl-5-methoxypyridineHCID 670476742-Fluoro-5-iodo-N-methylbenzamide

Product 1

HCID 670480172-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-N-methylbenzamideYield 73%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178419050HCID 178419050, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

Add bis(triphenylphosphine)palladium (II) dichloride (64 mg, 0.091 mmol), copper (I) iodide (35 mg, 0.19 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (250 mg, 1.9 mmol) to a solution of 2-fluoro-5-iodo-N-methylbenzamide, (prepared as described in PREPARATION 39), (0.63 g, 2.3 mmol) in triethylamine (3.8 mL, 27.3 mmol) and heat at 60° C. for 16 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100:0 to 10:90 dichloromethane:ethyl acetate, followed by a second silica gel chromatography eluting with 50:50 to 75:25 ethyl acetate:hexanes, to give the title compound as a white solid (390 mg, 73%).

Workup

  1. temperatureCool to room temperature
  2. concentrationconcentrate
  3. customPurify by silica gel chromatography
  4. washeluting with 100:0 to 10:90 dichloromethane
  5. washeluting with 50:50 to 75:25 ethyl acetate

Sources & evidence

ORD record
ord-3a7a95c0274745b6acf7bd43e1d02e2a
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915424B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes