Sodium Carbonate → HCID 66790536, compound

HRID 2422546Notes

Reaction equation

HRID 2422546 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH:17]=[C:16]([C:18]([OH:25])([C:21]([F:24])([F:23])[F:22])[CH2:19][CH3:20])[N:15]=[N:14]3)=[CH:9][CH:10]=2)[N:5]=[C:4]([C:26]#[N:27])[CH:3]=1.[F:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:34]=1[F:35].C([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:28][C:29]1[CH:30]=[C:31]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([CH2:12][N:13]4[CH:17]=[C:16]([C@:18]([OH:25])([C:21]([F:22])([F:24])[F:23])[CH2:19][CH3:20])[N:15]=[N:14]4)=[CH:9][CH:10]=3)[N:5]=[C:4]([C:26]#[N:27])[CH:3]=2)[CH:32]=[CH:33][C:34]=1[F:35]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 59774876HCID 59774876, compound

Product 1

HCID 66790536HCID 66790536, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-chloro-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carbonitrile (100 mg, 0.25 mmol) in DME (3 mL) was added tetrakis(triphenylphosphine)palladium (14 mg, 0.013 mmol), 3,4-difluorophenylboronic acid (59 mg, 0.38 mmol) and aq. 2M Na2CO3 (0.38 mL, 0.75 mmol). After 2 h at 100° C., the reaction was quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with EtOAc/hexanes, 4:6) gave the title compound. MS (+ESI): 474 (M+H)+.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel (eluting with EtOAc/hexanes, 4:6)

Sources & evidence

ORD record
ord-a462244c208d47e2b617fc2f86f20c15
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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