Diethyl Ether → HCID 9821880, compound

HRID 2300849Notes

Reaction equation

HRID 2300849 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([Sn](CCCC)(CCCC)CCCC)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1.CCOCC.C(OCC)(=O)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:39]5[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 122863-BromopyridineHCID 69961490HCID 69961490, compound

Product 1

HCID 9821880HCID 9821880, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of 2-[(S)-1-phenylethylamino]-4-[5-(tributylstannyl)-benzimidazol-1-yl]pyrimidine (27 mg), 3-bromopyridine (44 μL) and tetrakis(triphenylphosphine)palladium(0) (0.5 mg) in DMF (4 mL) was heated and maintained at 100° C. overnight. The reaction mixture was cooled and transferred to a separatory funnel containing 100 mL ether plus 25 mL ethyl acetate. The organic layer was washed 3× with water and 1× with brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The product was purified by silica gel chromatography eluting with methanol in dichloromethane to give 9.1 mg of the title compound. Mass spectrum (ESI): 393.2 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customtransferred to a separatory funnel
  3. washThe organic layer was washed 3× with water and 1× with brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by silica gel chromatography
  8. washeluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-e8101305cc544999b395389e5499c89d
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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