3-(2,6-difluoropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine → HCID 178511598, compound

HRID 68344Notes

Reaction equation

HRID 68344 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[C:4]([F:17])[N:3]=1.[C@H:18]1([NH2:25])[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]1>C(O)C>[F:17][C:4]1[N:3]=[C:2]([NH:24][C@H:21]2[CH2:22][CH2:23][C@H:18]([NH2:25])[CH2:19][CH2:20]2)[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 674419563-(2,6-difluoropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridineHCID 178511674HCID 178511674, compound

Product 1

HCID 178511598HCID 178511598, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of EXAMPLE 56B (0.60 g, 2.60 mmol) and trans-cyclohexane-1,4-diamine (1.04 g, 9.08 mmol) in ethanol (10 mL) was heated at in a Biotage Initiator microwave reactor at 170° C. for 80 minutes. After concentration, the residue was treated with 20% brine and extracted twice with ethyl acetate. The combined organic layers were concentrated and purified on a 110 g silica column (KP-NH from Biotage) eluting with ethyl acetate/methanol (97:3 to 90:10) to give the title compound.

Workup

  1. concentrationAfter concentration
  2. additionthe residue was treated with 20% brine
  3. extractionextracted twice with ethyl acetate
  4. concentrationThe combined organic layers were concentrated
  5. custompurified on a 110 g silica column (KP-NH from Biotage)
  6. washeluting with ethyl acetate/methanol (97:3 to 90:10)

Sources & evidence

ORD record
ord-a14def5fc1f34ae78a51f4254de8dfae
Source dataset
uspto-grants-2014_09
Patent number
US08822446B2

Reaction notes

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