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Toluene → HCID 44197809, compound

HRID 1969103
Notes
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Reaction equation

HRID 1969103 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(B(O)O)CCCCC=1.C(=O)([O-])[O-].[K+].[K+]>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(O)C>[C:18]1([C:2]2[CH:3]=[C:4]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 38629021-Cyclohexenylboronic acidHCID 57786669HCID 57786669, compound

Product 1

HCID 44197809HCID 44197809, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-pyridin-2-yl-amine (0.063 g, 0.26 mmol), 2 mL of toluene, 0.5 mL of ethanol, cyclohexen-1-yl boronic acid (0.065 g, 0.51 mmol), Pd(PPh3)4 (0.032 g, 0.027 mmol), and 0.36 mL of a 2 M aq. potassium carbonate solution under N2 was stirred at 170° C. in a microwave for 3 h. The mixture was partitioned between 10 mL of a 10% NaOH solution and 10 mL of dichloromethane. The aqueous layer was further extracted with 10 mL of dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to 0.093 g of a pale yellow oil. Column chromatography (0->33% EtOAc/hexanes) afforded 0.050 g (66%) of (6-cyclohex-1-enyl-imidazo[1,2-b]pyridazin-8-yl)-pyridin-2-yl-amine as a white solid.

Workup

  1. customThe mixture was partitioned between 10 mL of a 10% NaOH solution and 10 mL of dichloromethane
  2. extractionThe aqueous layer was further extracted with 10 mL of dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to 0.093 g of a pale yellow oil

Sources & evidence

ORD record
ord-2388399d6eab4e20b8836f3f51f182cd
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426441B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes