Dichloromethane → 5-(2-Amino-4-methyl-pyrimidin-5-yl)-2-chloro-N-(5-trifluoromethyl-pyridin-2-yl)benzenesulfonamide

HRID 2382603Notes

Reaction equation

HRID 2382603 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.[CH3:23][C:24]1[C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=[C:26]([NH2:39])[N:25]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>C(OCC)(=O)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].COCCOC>[NH2:39][C:26]1[N:25]=[C:24]([CH3:23])[C:29]([C:2]2[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([S:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=3)(=[O:10])=[O:9])[CH:7]=2)=[CH:28][N:27]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 529879064-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amine2×HCID 687257695-bromo-2-chloro-N-(5-trifluoromethyl-pyridin-2-yl)-benzenesulfonamide

Product 1

HCID 687237395-(2-Amino-4-methyl-pyrimidin-5-yl)-2-chloro-N-(5-trifluoromethyl-pyridin-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 5 ml microwave tube is charged with 5-bromo-2-chloro-N-(5-trifluoromethyl-pyridin-2-yl)-benzenesulfonamide (0.067 g, 0.16 mmol) and DME (degassed 3 ml), 4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-pyrimidin-2-ylamine (Intermediate G) (0.0535 g, 0.19 mmol), 2 M aqueous Na2CO3 solution (640 μl) and PdCl2(dppf).DCM (0.00448 g, 5.4 μmol) and the mixture is heated using microwave radiation at 110° C. for 15 min. After cooling to room temperature the mixture is taken up in ethyl acetate (50 ml), washed with water, dried over MgSO4 and concentrated in vacuo. The crude product is triturated with DCM (0.5 ml), filtrated and washed with DCM to afford the pure title compound.

Workup

  1. customat 110° C.
  2. customfor 15 min
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is triturated with DCM (0.5 ml)
  7. filtrationfiltrated
  8. washwashed with DCM

Sources & evidence

ORD record
ord-6b6d2136624e430eb62b7c2febbbd851
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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