Water → HCID 11698872, compound

HRID 1437757Notes

Reaction equation

HRID 1437757 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH:5]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:32][S:33]([C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1)(=[O:35])=[O:34].O>O1CCOCC1.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>[CH3:32][S:33]([C:36]1[CH:41]=[C:40]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH:5]=[C:4]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:3]=2)[CH:39]=[CH:38][CH:37]=1)(=[O:35])=[O:34]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 11717717HCID 11717717, compound

Product 1

HCID 11698872HCID 11698872, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (6-chloro-4-morpholin-4-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amine (75 mg, 0.20 mmol) in 1,4-dioxane (8 mL) were added 2N sodium carbonate solution (0.5 mL) and tetrakis(triphenylphosphine)palladium(0) (11.6 mg, 0.010 mmol), followed by 3-methanesulfonyl phenyl boronic acid (48 mg, 0.24 mmol). The resulting reaction mixture was refluxed for 8 hours, after which time water was added (100 mL) to the reaction mixture, and the product was extracted with ethyl acetate (100 mL×3). The organic layer was dried over sodium sulphate, filtered, and the filtrate was concentrated under vacuum. The resulting product was purified by column chromatography using 230-400 mesh silica gel (elution 2:98 methanol:DCM) to afford the desired compound pale yellow solid (30 mg, yield 30%.).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 8 hours
  3. extractionthe product was extracted with ethyl acetate (100 mL×3)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe resulting product was purified by column chromatography

Sources & evidence

ORD record
ord-a5c316ba086a4f5a91d35f168937e5c8
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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