Sodium Carbonate → HCID 67319132, compound

HRID 1711598Notes

Reaction equation

HRID 1711598 reaction equation
C[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]3[CH2:16][C@H:15]3[NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.BrC1C=NC=C([F:31])C=1.CC1(C)C(C)(C)OB(C2C=CC([C@@H]3C[C@H]3NS(C(C)C)(=O)=O)=CC=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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.[Pd].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:31][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]3[CH2:16][C@H:15]3[NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:10][CH:9]=2)[CH:6]=[N:7][CH:2]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 8202063-Bromo-5-fluoropyridineHCID 67319244HCID 67319244, compound2×HCID 67319277HCID 67319277, compound

Product 1

HCID 67319132HCID 67319132, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 178527696HCID 178527696, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A similar procedure was followed as set out above for trans-N-{-2-[4-(6-methyl-3-pyridinyl)phenyl]cyclopropyl}-2-propanesulfonamide racemic (Example 2) using 3-bromo-5-fluoropyridine (66.5 mg, 0.378 mmol), trans-N-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}-2-propanesulfonamide (Intermediate 8) (69 mg, 0.189 mmol) in dry 1,4-dioxane (1.0 ml), polymer supported Tetrakis palladium catalyst (Pol-Pd(PPh3)4) (51 mg, 0.00567 mmol) and Na2CO3 2M (0.236 ml, 0.472 mmol) to give a crude product which was purified by reverse phase HPLC to give the title compound. The HPLC conditions were as given in “Preparative Chromatography” above.

Workup

  1. customto give a crude product which
  2. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-be17037fe19742d8b2d17e8afe566c74
Source dataset
uspto-grants-2010_09
Patent number
US07790758B2

Reaction notes

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