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Sodium Carbonate → HCID 90408168, compound

HRID 594064
Notes
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Reaction equation

HRID 594064 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:8])[N:5]=[N:6][CH:7]=1.[CH3:9][C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:8][C:4]1[N:5]=[N:6][CH:7]=[C:2]([C:11]2[CH:12]=[C:13]([NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=3)[CH:14]=[N:15][C:10]=2[CH3:9])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 565877855-Bromo-3-chloropyridazineHCID 90408605HCID 90408605, compound

Product 1

HCID 90408168HCID 90408168, compound

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
108 °C

Procedure

A mixture of 5-bromo-3-chloropyridazine (1.0 equiv.), N-(6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-3-(trifluoromethyl)benzamide (1.2 equiv.), sodium carbonate (2 M, 8 equiv.) and PdCl2(dppf) (0.5 equiv.) in DME (0.1 M) were heated to 108° C. for 13 min in the microwave. After removing the DME soluble portion and concentrating, the resulting solid was partitioned between EtOAc and water. The organic phase was washed with brine and then dried over sodium sulfate. After concentration, the crude material was purified via preparative reverse phase HPLC. Volatiles were removed by rotary evaporation and the remaining aqueous solution was basified with sodium bicarbonate. This solution was extracted with EtOAc, washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give crude N-(5-(6-chloropyridazin-4-yl)-6-methylpyridin-3-yl)-3-(trifluoromethyl)benzamide and was used in the next step without further purification. LCMS (m/z) (M+H)=393.1, Rt=0.73 min.

Workup

  1. customAfter removing the DME soluble portion
  2. concentrationconcentrating
  3. customthe resulting solid was partitioned between EtOAc and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationAfter concentration
  7. customthe crude material was purified via preparative reverse phase HPLC
  8. customVolatiles were removed by rotary evaporation
  9. extractionThis solution was extracted with EtOAc
  10. washwashed with brine
  11. dry with materialdried over sodium sulfate
  12. concentrationThe solution was concentrated
  13. customdried under vacuo

Sources & evidence

ORD record
ord-7bbcb49a999b4ac5bd9240cc0d688a9c
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242969B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes