Potassium Carbonate → HCID 67407131, compound

HRID 340788Notes

Reaction equation

HRID 340788 reaction equation
[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:19])[C:15](I)=[C:16]([F:17])[C:11]=3[N:10]=[C:9]2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29][CH3:30])=[O:28])[CH2:22]2)=[CH:3][CH:2]=1.[C:37]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.C([O-])([O-])=O.[K+].[K+]>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.CN(C=O)C>[C:37]1([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:42]=[CH:41][C:40]([C:15]2[C:14]([F:19])=[CH:13][C:12]3[N:8]([CH2:7][C:4]4[CH:3]=[CH:2][C:1]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:6][CH:5]=4)[C:9]([O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29][CH3:30])=[O:28])[CH2:22]4)=[N:10][C:11]=3[C:16]=2[F:17])=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 71073856HCID 71073856, compound

Product 1

HCID 67407131HCID 67407131, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A 50 mL flask was charged with methyl 3-{[1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1H-benzimidazol-2-yl]oxy}cyclohexanecarboxylate (0.4 g, 0.664 mmol), 4-biphenylboronic acid (0.130 g, 0.664 mmol), Pd(PPh3)4 (0.038 g, 0.033 mmol), DMF (9 mL), and 1 M aqueous K2CO3 (1.3 ml, 1.30 mmol). The reaction was degassed with N2 and then heated at 120° C. for 1 h. Then the volatiles were removed in vacuo and the resulting residue was partitioned between EtOAc and H2O. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. Chromatography of the resulting residue over silica (preparative TLC) eluting with 40% EtOAc/hexanes afforded the title compound. LC-MS: calculated for C40H34F2N2O3 628.25, observed m/e: 629.17 (M+H)+ (Rt 3.83/4 min).

Workup

  1. customThe reaction was degassed with N2
  2. customThen the volatiles were removed in vacuo
  3. customthe resulting residue was partitioned between EtOAc and H2O
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washChromatography of the resulting residue over silica (preparative TLC) eluting with 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-8212bfa7cbab41a79e7aa25a5764ea8b
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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