Water → HCID 18752900, compound

HRID 1838078Notes

Reaction equation

HRID 1838078 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[O:10]1[C:14]2[CH:15]=[CH:16][C:17](/[CH:19]=[CH:20]/[Sn](CCCC)(CCCC)CCCC)=[CH:18][C:13]=2[O:12][CH2:11]1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>CN(C=O)C.C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:10]1[C:14]2[CH:15]=[CH:16][C:17](/[CH:19]=[CH:20]/[C:2]3[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=3)=[CH:18][C:13]=2[O:12][CH2:11]1

Participants

8

Reactant 4

HCID 962WaterHCID 80271Tri-o-tolylphosphineHCID 27639713-Bromo-5-chloropyridin-2-amineHCID 18752878HCID 18752878, compound

Product 1

HCID 18752900HCID 18752900, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-bromo-5-chloro-2-pyridinamine (318 mg, 1.5 mmol), [(E)-2-(1,3-benzodioxol-5-yl)ethenyl](tributyl)stannane (250 mg, 1.7 mmol) (A. J. Bridges, A. Lee, C. E. Schwatrz, M. J. Towle, B. A. Littlefield, Bioorg. Med. Chem., 1993, 1, 403), palladium acetate (19 mg, 0.08 mmol) and tri-o-tolylphosphine (50 mg, 0.16 mmol) in DMF (0.5 ml) and triethylamine (0.5 ml) in a teflon pressure vessel was heated in a microwave (full power) for 20 sec, allowed to cool to RT heated in a microwave for a further 20 sec and then 1 min 20 sec. After allowing to cool, the reaction mixture was poured into water (20 ml) and extracted with EtOAc (3×20 ml). The combined extracts were washed with water (2×20 ml), dried over MgSO4 and concentrated. Recrystallisation from EtOAc—hexane gave the title compound as a brown solid (170 mg, 0.6 mmol):

Workup

  1. temperatureheated in a microwave for a further 20 sec
  2. custom1 min 20 sec
  3. temperatureto cool
  4. extractionextracted with EtOAc (3×20 ml)
  5. washThe combined extracts were washed with water (2×20 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customRecrystallisation from EtOAc—hexane

Sources & evidence

ORD record
ord-567c847ae5ef460297a6cd9d5c45f531
Source dataset
uspto-grants-2004_01
Patent number
US06673789B2

Reaction notes

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