Sodium Carbonate → HCID 86761274, compound

HRID 1362903Notes

Reaction equation

HRID 1362903 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=3[F:22])[C@@H:10]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:9]2)=[CH:4][CH:3]=1.[F:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[N:7]=[N:6][C:5]([N:8]3[CH2:13][CH2:12][C@H:11]([C:14]4[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=4[F:22])[C@@H:10]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:9]3)=[CH:4][CH:3]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86761275HCID 86761275, compound

Product 1

HCID 86761274HCID 86761274, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 58 mg (0.12 mmol) of the product of Step A and 27 mg (0.19 mmol) of 4-fluorophenylboronic acid in 4 mL of 1:1 ethanol/toluene was added 0.60 mL (1.2 mmol) 2N aqueous sodium carbonate solution followed by 200 mg (0.245 mmol) of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (II). The resulting solution was stirred under nitrogen at 100° C. for 24 h, then allowed to cool to ambient temperature. The reaction mixture was then filtered through a pad of Celite and the filter cake washed with ethyl acetate and methanol. The combined filtrate and washings were concentrated and the crude material was purified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 10 to 90% acetonitrile/water with 0.1% TFA) to afford the title compound as a yellow oil. LC/MS 537.3 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationThe reaction mixture was then filtered through a pad of Celite
  3. washthe filter cake washed with ethyl acetate and methanol
  4. concentrationThe combined filtrate and washings were concentrated
  5. customthe crude material was purified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 10 to 90% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-77841864b88644fe80fc70c4b546ad18
Source dataset
uspto-grants-2011_02
Patent number
US07884104B2

Reaction notes

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