Sodium Carbonate → HCID 25118020, compound

HRID 869931Notes

Reaction equation

HRID 869931 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:4][C:3]=1[CH3:25].[CH3:26][O:27][C:28]1[N:33]=[CH:32][C:31](B(O)O)=[C:30](C)[CH:29]=1.[C:38]([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[F:21][C:19]1([F:22])[O:18][C:17]2[CH:23]=[CH:24][C:14]([C:11]3([C:9]([NH:8][C:6]4[N:7]=[C:2]([C:29]5[C:28]([O:27][CH3:26])=[N:33][CH:32]=[C:31]([CH3:38])[CH:30]=5)[C:3]([CH3:25])=[CH:4][CH:5]=4)=[O:10])[CH2:13][CH2:12]3)=[CH:15][C:16]=2[O:20]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27630832-Methoxy-4-methylpyridine-5-boronic acidHCID 59165796N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide

Product 1

HCID 25118020HCID 25118020, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (0.550 g, 1.5 mmol) and 6-methoxy-4-methylpyridin-3-ylboronic acid (0.376 g, 2.25 mmol) in DME (10 mL) and Na2CO3 (2 M, 1.5 mL, 3.0 mmol) was added Pd(PPh3)4 (0.087 g, 0.075 mmol). The mixture was heated in microwave oven at 120° C. for 30 minutes. The reaction was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were washed with brine and dried over MgSO4. After the removal of solvent, the residue was purified by column chromatography (0-20% EtOAc-Hexane) to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(2′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (0.554 g, 81%). ESI-MS m/z calc. 453.44. found 454.2 (M+1)+. Retention time 2.08 minutes.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. extractionthe aqueous layer was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customAfter the removal of solvent
  6. customthe residue was purified by column chromatography (0-20% EtOAc-Hexane)

Sources & evidence

ORD record
ord-f09800a04a234c95813e9296cc5c868d
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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