Potassium Carbonate → HCID 68083968, compound

HRID 1470356

Reaction equation

HRID 1470356 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[O:10][C:3]=12.[NH2:23][CH2:24][C:25]1[C:26]([N:31]([CH3:36])[S:32]([CH3:35])(=[O:34])=[O:33])=[N:27][CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:36][N:31]([C:26]1[C:25]([CH2:24][NH:23][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[O:10][C:3]=23)=[CH:30][CH:29]=[CH:28][N:27]=1)[S:32]([CH3:35])(=[O:34])=[O:33]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 45480403N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamideHCID 667789647-Chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine

Product 1

HCID 68083968HCID 68083968, compoundYield 34%

Conditions

Temperature
110 °C

Procedure

To a dry 10 mL microwave vial with stirbar was added 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine (50.00 mg; 0.16 mmol; 1.00 eq.), N-(3-aminomethyl-pyridin-2-yl)-N-methyl-methanesulfonamide (40.40 mg; 0.19 mmol; 1.20 eq.), chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-tert.-butyl ether adduct (2.59 mg; 0.003 mmol; 0.02 eq.), and potassium carbonate (30.26 mg; 0.22 mmol; 1.40 eq.). The vial was sealed and flushed with N2. The reagents were suspended in tert.-BuOH (1.00 ml) and the reaction mixture was heated to 110° C. with stirring for 1 h. The reaction mixture was cooled to room temperature and concentrated on a rotary evaporator. The crude mixture was purified by Biotage chromatography (20-100% EtOAc/hex KP-NH SNAP column) to afford the title compound as a beige solid (27 mg, 34%). (HPLC (method F): 90%, RT: 4.62 min); MS (m/z) 499 [M+H]+, RT: 2.5 min.

Workup

  1. customThe vial was sealed
  2. customflushed with N2
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated on a rotary evaporator
  5. customThe crude mixture was purified by Biotage chromatography (20-100% EtOAc/hex KP-NH SNAP column)

Sources & evidence

ORD record
ord-c3fa383a1ed44681a79c7a72f1962aed
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Linked notes

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