HCID 90093879, compound → HCID 118344727, compound

HRID 1753043Notes

Reaction equation

HRID 1753043 reaction equation
I[C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=1.[Li]CCCC.[CH3:19][O:20][C:21]1[C:26]([N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][C:24]([C:42](=[O:47])N(OC)C)=[CH:23][N:22]=1>CCOCC>[CH:11]([N:4]1[C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:2]([C:42]([C:24]2[CH:25]=[C:26]([N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[C:21]([O:20][CH3:19])=[N:22][CH:23]=2)=[O:47])=[CH:3]1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 90093879HCID 90093879, compoundHCID 118344726HCID 118344726, compoundHCID 178418339Butyllithium

Product 1

HCID 118344727HCID 118344727, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3-iodo-1-isopropyl-1H-pyrrolo[3,2-c]pyridine (Preparation 45, 250 mg, 0.875 mmol) in ether (5 mL) at −78° C. was added nBuLi (2.3M in hexane, 0.38 mL, 0.875 mmol) and the reaction stirred at this temperature for 30 minutes. A solution of di-tert-butyl {2-methoxy-5-[methoxy(methyl)carbamoyl]pyridin-3-yl}imidodicarbonate (Preparation 69, 300 mg, 0.729 mmol) in ether (2 mL) was added and the reaction continued to stir at this temperature for another 30 minutes. The reaction was warmed to room temperature for 2 hours before being quenched by the addition of saturated ammonium chloride solution. The reaction was extracted into EtOAc (3×15 mL), the combined organic layers were washed with water (15 mL), brine (15 mL), dried over sodium sulphate and concentrated in vacuo. The residue was purified using preparative TLC eluting with EtOAc:DCM 50:50 to afford the title compound and taken on to the next step directly.

Workup

  1. stirringto stir at this temperature for another 30 minutes
  2. custombefore being quenched by the addition of saturated ammonium chloride solution
  3. extractionThe reaction was extracted into EtOAc (3×15 mL)
  4. washthe combined organic layers were washed with water (15 mL), brine (15 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with EtOAc:DCM 50:50

Sources & evidence

ORD record
ord-d59dde1f94274cd19ee1a12eceacf641
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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