2-Bromopyridine → HCID 20041079, compound

HRID 1762460Notes

Reaction equation

HRID 1762460 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[C:13]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[CH:17][C:16]([C:19]2([C:23]#[N:24])[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.O1CCCC1>CCOCC.CCCCCC.O.CO>[C:13]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:14]=[CH:15][C:16]([C:19]2([C:23]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)=[NH:24])[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:18]=1

Participants

9

Reactant 4

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 20041059HCID 20041059, compoundHCID 178418339Butyllithium

Product 1

HCID 20041079HCID 20041079, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 2-bromopyridine (4.8 g) in dry ether (30 ml) was added to a 1.7M solution of butyllithium in hexane (18 ml) at -78° C. with stirring. After one hour at that temperature a solution of 1-(4-biphenylyl)cyclobutanecarbonitrile (4 g) in a mixture of dry ether (80 ml) and dry tetrahydrofuran (10 ml) was added and the temperature allowed to rise to 0° C. After cooling to -20° C., methanol (20 ml) and then water (30 ml) were added dropwise. The aqueous mixture was extracted with ether and the ether extract washed, dried and evaporated to give [1-(4-biphenylyl)cyclobutyl](pyrid-2-yl)methanimine as an orange oil. The oil was dissolved in propan-2-ol (200 ml) and heated under reflux with sodium borohydride (2.0 g) for five hours. Water was added and the propan-2-ol removed by evaporation. The aqueous residue was extracted with ether. Hydrogen chloride gas was passed into the dried ether extract to give a gum which was heated with propan-2-ol to give a white solid which was recrystallised from a mixture of methanol and propan-2-ol to give [1-(4-biphenylyl)cyclobutyl](pyrid-2-yl)methylamine dihydrochloride hydrate (m.p. 240° C. (dec)).

Workup

  1. additionwas added
  2. customto rise to 0° C
  3. extractionThe aqueous mixture was extracted with ether
  4. extractionthe ether extract
  5. washwashed
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-64cc4f64af3c42d8b55e11987627a0a1
Source dataset
uspto-grants-1989_05
Patent number
US04833143

Reaction notes

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