Dichloromethane → HCID 68726668, compound

HRID 2382601Notes

Reaction equation

HRID 2382601 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]=1[S:17]([NH:20][CH:21]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]1)(=[O:19])=[O:18].Br[C:29]1[C:30]([CH3:36])=[N:31][C:32]([NH2:35])=[N:33][CH:34]=1.C(Cl)Cl>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]>[NH2:35][C:32]1[N:31]=[C:30]([CH3:36])[C:29]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([S:17]([NH:20][CH:21]3[CH2:22][CH2:23][CH:24]([OH:27])[CH2:25][CH2:26]3)(=[O:18])=[O:19])[CH:4]=2)=[CH:34][N:33]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 186161965-Bromo-4-methylpyrimidin-2-amine2×HCID 68725034HCID 68725034, compound

Product 1

HCID 68726668HCID 68726668, compound

Reagents, catalysts & solvents 1

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

Procedure

The crude 2-chloro-N-(4-hydroxy-cyclohexyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide from step 2 (1.48 g), 5-Bromo-4 methyl-pyrimidin-2-ylamine (intermediate C) (0.669 g, 3.36 mmol) and PdCl2(dppf).DCM (0.436 g, 0.53 mmol) are placed in a microwave vial containing degassed DME (10 ml) and 2M Na2CO3 (2 ml). The resulting mixture is heated using microwave radiation at 100° C. for 15 minutes. After evaporation of the solvent, the reaction mixture is purified by flash chromatography on silica eluting with ethanol to afford the title compound.

Workup

  1. additioncontaining
  2. customdegassed DME (10 ml) and 2M Na2CO3 (2 ml)
  3. temperatureThe resulting mixture is heated
  4. customat 100° C.
  5. customfor 15 minutes
  6. customAfter evaporation of the solvent
  7. customthe reaction mixture is purified by flash chromatography on silica eluting with ethanol

Sources & evidence

ORD record
ord-2589e88dee3c42d489122ba2bc8d1f99
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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