Potassium Phosphate, Tribasic → HCID 86728224, compound

HRID 1776794Notes

Reaction equation

HRID 1776794 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.C(OC([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1B(O)O)=O)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:10][C:4]1[N:3]=[C:2]([C:19]2[NH:18][C:26]3[C:21]([CH:20]=2)=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:7]([O:8][CH3:9])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 717433362,6-Dichloro-3-methoxypyridine

Product 1

HCID 86728224HCID 86728224, compoundYield 69.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a degassed solution of compound 2,6-dichloro-3-methoxypyridine (8.9 g, 0.05 mol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (13 g, 0.05 mol) and K3PO4 (31.8 g, 3.0 mol) in DMF (100 mL) was added Pd(dppf)Cl2 (3.65 g, 5 mmol) under N2. The mixture was heated at 60° C. for about 15 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc and filtered. The filtrate was washed with H2O, brine, dried over Na2SO4. After being concentrated in vacuo, the resulting resulting residue was purified using prep-HPLC to provide the desired product of 2-(6-chloro-3-methoxypyridin-2-yl)-1H-indole (9.0 g, yield: 69.8%). 1H-NMR (CDCl3, 400 MHz) δ 9.52 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.38˜7.43 (m, 2H), 7.07˜7.26 (m, 4H), 4.03 (s, 3H). MS (M+H)+: 259/261.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter being concentrated in vacuo
  6. customthe resulting resulting residue
  7. customwas purified

Sources & evidence

ORD record
ord-3f9a02eb11a747078ca15bfd777101a4
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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