Tetrahydrofuran → HCID 71140765, compound

HRID 629923Notes

Reaction equation

HRID 629923 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:16])[C:9](=[O:15])[N:10]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:5]2=[CH:4][CH:3]=1.[CH3:17]C(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[Br-].[CH2:52]([O:54][C:55](=[O:59])[CH2:56][CH2:57][Zn+])C.C1COCC1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][C:12]([CH3:13])([CH3:14])[CH2:11][N:10]1[C:5]2[C:6](=[N:7][C:2]([CH2:57][CH2:56][C:55]([O:54][CH3:52])=[O:59])=[CH:3][CH:4]=2)[N:8]([CH3:16])[C:9]1=[O:15]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 772308275-chloro-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 178471816HCID 178471816, compound

Product 1

HCID 71140765HCID 71140765, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1-4 (0.10 g, 0.39 mmol), Pd(OAc)2 (0.004 g, 0.02 mmol), xphos (0.02 g, 0.039 mmol) in dioxane (3 mL) was added 3-ethoxy-3-oxopropylzinc bromide 0.5M solution in THF (3.15 mL, 1.57 mmol) and the resulting mixture was microwave irradiated for 30 minutes at 100° C. The reaction was allowed to cool and partitioned between ethyl acetate and water. The organic phase was concentrated and flash column separation using a 0-30% ethyl acetate/hexane gradient gave 37-1. (0.10 g, 86%). LRMS (ES) (M+H)+: observed=320.1, calculated=320.4.

Workup

  1. customthe resulting mixture was microwave irradiated for 30 minutes at 100° C
  2. temperatureto cool
  3. custompartitioned between ethyl acetate and water
  4. concentrationThe organic phase was concentrated
  5. customflash column separation
  6. customgave 37-1

Sources & evidence

ORD record
ord-30f308f0374141b58baad62accb26015
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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