Tetrahydrofuran → Ammonium hydroxide methanol

HRID 1618795Notes

Reaction equation

HRID 1618795 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br-].[CH:15]1([Zn+])[CH2:17][CH2:16]1.C1C[O:22][CH2:21]C1>C1(C)C=CC=CC=1.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:21][OH:22].[NH4+:3].[OH-:22].[Cl:13][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH:15]2[CH2:17][CH2:16]2)[C:11]=1[CH3:12]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 220826612,4-Dichloro-3-methyl-1,8-naphthyridineHCID 178419765HCID 178419765, compound

Product 2

HCID 21894508Ammonium hydroxide methanolHCID 66631833HCID 66631833, compound

Reagents, catalysts & solvents 2

HCID 178478230HCID 178478230, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2,4-dichloro-3-methyl-1,8-naphthyridine (210 mg, 0.986 mmol) in toluene (5 mL) was added dichloro 1,1′-bis(diphenylphosphino)-ferrocene palladium (II) (161 mg, 0.197 mmol), cyclopropylzinc bromide solution 0.5 m in THF (3.94 mL, 1.971 mmol). The reaction was heated at 100° C. for 2 h. After this time the reaction was cooled to rt and partitioned between EtOAc (60 mL) and water (20 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (DCM/DCM:—MeOH:NH4OH (9:1:0.4), 1:0 to 7:3 as eluent) gave 4-chloro-2-cyclopropyl-3-methyl-1,8-naphthyridine. Mass Spectrum (ESI) m/e=219.2.

Workup

  1. temperatureAfter this time the reaction was cooled to rt
  2. custompartitioned between EtOAc (60 mL) and water (20 mL)
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3f169930ee0e48efbe5b089ab26b4982
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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