Cesium carbonate → HCID 66582331, compound

HRID 1972528Notes

Reaction equation

HRID 1972528 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:18][C:19]([F:39])([F:38])[C:20]([C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][CH:24]=1)([OH:22])[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:17][C:14]1[N:15]=[CH:16][C:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([C:26]3[CH:27]=[CH:28][C:23]([C:20]([OH:22])([CH3:21])[C:19]([F:38])([F:39])[F:18])=[CH:24][CH:25]=3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 58347286HCID 58347286, compoundHCID 66582681HCID 66582681, compound

Product 1

HCID 66582331HCID 66582331, compoundYield 85.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A 10 mL vial was charged with 5-((4-bromophenyl)sulfonyl)-2-pyridinamine (71 mg, 0.23 mmol), 1,1,1-trifluoro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol (86 mg, 0.27 mmol, synthesized in manner analogous to Example 21 using 2-(4-bromophenyl)-1,1,1-trifluoro-2-propanol (example 27)), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride, dichloromethane complex (18 mg, 0.02 mmol, Sigma-Aldrich, St. Louis, Mo.), and cesium carbonate (222 mg, 0.68 mmol) were combined in DME (1.2 mL) and water (0.1 mL). The reaction mixture was purged with nitrogen for several minutes, and then stirred and heated in an Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 30 min. The organic layer was taken and the solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by column chromatography (12 g of silica gel, 0 to 3% 2M NH3 in MeOH/CH2Cl2) to provide 2-(4′-((6-amino-3-pyridinyl)sulfonyl)-4-biphenylyl)-1,1,1-trifluoro-2-propanol (83 mg) as an off-white solid.

Workup

  1. customThe reaction mixture was purged with nitrogen for several minutes
  2. customthe solvent was removed under reduced pressure
  3. customThe crude material was absorbed onto a plug of silica gel
  4. custompurified by column chromatography (12 g of silica gel, 0 to 3% 2M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-440aa9f485ad4e039c3cf54dc194e15f
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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