Sodium Carbonate → HCID 25025698, compound

HRID 417825Notes

Reaction equation

HRID 417825 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH:9]2[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=3)(=[O:17])=[O:16])[CH2:10]2)[C:4](=[O:25])[N:3]=1.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.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]>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH:9]2[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]3[CH:19]=[C:20]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[F:26])[CH:21]=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH2:10]2)[C:4](=[O:25])[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 66649340HCID 66649340, compound

Product 1

HCID 25025698HCID 25025698, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-[3-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl]-3-bromo-benzenesulfonamide (66 mg, 0.153 mmol) in acetonitrile (2.5 mL), 2-fluorophenylboronic acid (35 mg, 0.25 mmol), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium (20 mg, 0.024 mmol) and 2M Na2CO3 solution (2.5 mL) were added, the mixture was stirred for 30 seconds. The reaction was completed by microwave at 120° C. for ten minutes. The organic phase of the reaction mixture was filtered and purified by a reverse phase preparative HPLC, giving 26 mg (38%) 2′-fluoro-biphenyl-3-sulfonic acid [3-(4-Amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl]-amide (6) as a white solid.

Workup

  1. waitThe reaction was completed by microwave at 120° C. for ten minutes
  2. filtrationThe organic phase of the reaction mixture was filtered
  3. custompurified by a reverse phase preparative HPLC

Sources & evidence

ORD record
ord-d7ad7de2b28946188b3bbdff4d279f46
Source dataset
uspto-grants-2012_01
Patent number
US08093245B2

Reaction notes

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