Nitrogen → HCID 66634522, compound

HRID 1810294Notes

Reaction equation

HRID 1810294 reaction equation
C([O:3][C:4](=[O:44])[CH2:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=2[CH2:30][N:31]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:32][CH3:33])[C:9](OS(C(F)(F)F)(=O)=O)=[CH:10][CH:11]=1)C.[C:45]1(B(O)O)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(=O)([O-])[O-].[K+].[K+].N#N>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.O.COCCOC>[CH2:37]([O:36][C:34]([N:31]([CH2:30][C:21]1[CH:22]=[C:23]([C:26]([F:29])([F:27])[F:28])[CH:24]=[CH:25][C:20]=1[C:8]1[C:9]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:3])=[O:44])[CH:7]=1)[CH2:32][CH3:33])=[O:35])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86662774HCID 86662774, compound

Product 1

HCID 66634522HCID 66634522, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of {2′-[(benzyloxycarbonyl-ethyl-amino)-methyl]-6-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester (0.11 g, 0.17 mmol), phenylboronic acid (0.023 g, 0.19mmol), and potassium carbonate (0.070 g, 0.51 mmol) in 2:1 DME:H2O (5 mL) was purged with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.02 mmol) was added, and the reaction was purged with N2 for another 10 minutes, and then stirred at 90° C. overnight. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound. M+H is 548.

Workup

  1. customthe reaction was purged with N2 for another 10 minutes
  2. customThe mixture was partitioned between EtOAc and H2O
  3. customthe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-14baaaa9d9964250a86a928aa1779be6
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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