Potassium Acetate → 3-(oxan-4-yl)-1H-pyrrolo[2,3-c]pyridine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH2:8].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])(=O)C.[K+].[O:48]1[CH2:53][CH2:52][CH:51]([CH2:54][CH:55]=O)[CH2:50][CH2:49]1>CC(N(C)C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:48]1[CH2:53][CH2:52][CH:51]([C:54]2[C:2]3[C:3](=[CH:4][N:5]=[CH:6][CH:7]=3)[NH:8][CH:55]=2)[CH2:50][CH2:49]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
4-Chloro-3-aminopyridine (200 mg, 1.56 mmol) was dissolved in DMA (4 mL) and Pd2(dba)3 (71.2 mg, 0.08 mmol), X-Phos (74.2 mg, 0.16 mmol), potassium acetate (458 mg, 4.67 mmol) and (tetrahydro-pyran-4-yl)-acetaldehyde (598 mg, 4.67 mmol) were added under nitrogen. The reaction mixture was heated at 120° C. overnight, cooled to r.t. and partitioned between water (100 mL) and DCM (100 mL). The aqueous fraction was concentrated in vacuo and the residue was dissolved in DCM (100 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound as an orange/brown solid (314 mg, 99.8%). LCMS (ES+): 203.1 (M+H)+.
Workup
- temperaturecooled to r.t.
- custompartitioned between water (100 mL) and DCM (100 mL)
- concentrationThe aqueous fraction was concentrated in vacuo
- dissolutionthe residue was dissolved in DCM (100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ab8d2e76df5c46e3b4be61c9c4facee0
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227967B2
Reaction notes
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