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

4-Chloroaniline → 1-(4-Chlorophenylamino)-4-(4-pyridylmethoxy)pyridazine

HRID 1070536
Notes
Print preview

Reaction equation

HRID 1070536 reaction equation
Br[N:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][NH:3]1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(OC(C)(C)C)(C)(C)C.[Na]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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]>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][N:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[CH:4][NH:3]2)=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 78124-ChloroanilineHCID 223972771-Bromo-4-(4-pyridylmethoxy)pyridazineHCID 86662868Sodium t-butyloxide

Product 1

HCID 223972801-(4-Chlorophenylamino)-4-(4-pyridylmethoxy)pyridazineYield 10%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To 1-bromo-4-(4-pyridylmethoxy)pyridazine (50 mg, 0.19 mmol) in toluene (3 mL) was added 4-chloroaniline (29 mg, 0.22 mmol), catalytical amount of (R)-(+)2,2′-bis(diphenyl phosphino)-1,1′-binaphthyl (1 mg), tris(dibenzylideneacetone)-dipalladium(0) (0.6 mg) and sodium t-butyloxide (26 mg, 0.27 mmol). The reaction mixture was heated at 80° C. for 12 h under argon. The reaction mixture became deep brown upon heating. The mixture was cooled to RT, diluted with ethyl acetate (10 mL), washed by brine and the organic layer was dried over Na2SO4, and the solvent was evaporated in vacuo. The crude mixture was purified by preparative thin layer plate to afford the title compound (6 mg, yield 10%). 1H-NMR (MeOH-4), 8.51 (d, 2H), 7.61(d, 2H) 7.52(dd, 2H), 7.15-7.25(m, 4H), 5.49(s, 2H); MS ES 313 (M+H)+, 315 (M+3H)+, 316 (M+4H)+, calc. 312; TLC (5:95 v/v methanol-methylene chloride) Rf=0.2.

Workup

  1. temperatureupon heating
  2. temperatureThe mixture was cooled to RT
  3. washwashed by brine
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customthe solvent was evaporated in vacuo
  6. customThe crude mixture was purified by preparative thin layer plate

Sources & evidence

ORD record
ord-ce55ff32496e413aa622f1323061cad3
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06903101B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes