Potassium Phosphate, Tribasic → HCID 69732978, compound

HRID 2182145Notes

Reaction equation

HRID 2182145 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19](Br)=[N:18][CH:17]=[C:16]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30]B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.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.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:30])=[N:18][CH:17]=[C:16]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 86588633HCID 86588633, compound

Product 1

HCID 69732978HCID 69732978, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3′-bromo-6′-(3-chloro-benzyloxy)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (I-3j) (82 mg, 0.17 mmol), methylboronic acid (15.3 mg, 0.25 mmol), K3PO4 (72 mg, 0.34 mmol), dppf (4.7 mg, 0.0085 mmol) and PdCl2dppf(CH2Cl2)2 (6.9 mg, 0.0085 mmol) in THF (anhydrous, 1.2 ml) under a nitrogen atmosphere was heated to reflux for 16 h. The reaction mixture was cooled to room temperature and filtered through a pad of silica gel, eluting with EtOAc-hexane (6:4). The filtrate was concentrated in vacuo. The residue was purified by preparative TLC (EtOAc-hexane 1:1) to provide 72 mg of the title compound I-3k (>99% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered through a pad of silica gel
  4. washeluting with EtOAc-hexane (6:4)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by preparative TLC (EtOAc-hexane 1:1)

Sources & evidence

ORD record
ord-f20057be49ee46b89fc597ee7b69aba0
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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