Dichloromethane → HCID 68724953, compound

HRID 2382596Notes

Reaction equation

HRID 2382596 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[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19].Br[C:28]1[C:29]([CH3:35])=[N:30][C:31]([NH2:34])=[N:32][CH:33]=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]>[NH2:34][C:31]1[N:30]=[C:29]([CH3:35])[C:28]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:17][S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:19])=[O:20])[CH:4]=2)=[CH:33][N:32]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 186161965-Bromo-4-methylpyrimidin-2-amine2×HCID 68723213HCID 68723213, compound2×

Product 1

HCID 68724953HCID 68724953, compound

Reagents, catalysts & solvents 1

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

Procedure

N-[2-Chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (Intermediate B) (50 mg, 0.13 mmol), 5-Bromo-4-methyl-pyrimidin-2-ylamine (Intermediate C) (26 mg, 0.14 mmol) and PdCl2(dppf).DCM (10 mg, 0.013 mmol) are placed in a microwave vial containing degassed DME (3 ml) and 2M Na2CO3 (1 ml). The resulting mixture is heated using microwave radiation at 100° C. for 45 minutes. The reaction mixture is diluted with DCM, MgSO4 is added and the mixture is filtered through Celite® (filter agent). The filtrate is absorbed onto silica and purification by flash chromatography on silica eluting with MeOH:DCM (1% to 2% MeOH) affords the title compound.

Workup

  1. additioncontaining
  2. customdegassed DME (3 ml) and 2M Na2CO3 (1 ml)
  3. temperatureThe resulting mixture is heated
  4. customat 100° C.
  5. customfor 45 minutes
  6. additionThe reaction mixture is diluted with DCM, MgSO4
  7. additionis added
  8. filtrationthe mixture is filtered through Celite® (filter agent)
  9. customThe filtrate is absorbed onto silica and purification by flash chromatography on silica eluting with MeOH

Sources & evidence

ORD record
ord-33e87df92a314abaa590bfe6d65751a1
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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