Sodium Carbonate → 3-(6'-Methylamino-[2,2';4',3'']terpyridin-5''-yl)-phenol

HRID 1798544Notes

Reaction equation

HRID 1798544 reaction equation
[C:1]([O-:4])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[C:18]([NH:20][CH3:21])[N:17]=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:15]=2)[CH:11]=[N:12][CH:13]=1>COCCOC.C(Cl)Cl.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]>[CH3:21][NH:20][C:18]1[N:17]=[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:15]=[C:14]([C:10]2[CH:11]=[N:12][CH:13]=[C:8]([C:8]3[CH:13]=[C:1]([OH:4])[CH:11]=[CH:10][CH:9]=3)[CH:9]=2)[CH:19]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 86633643(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-methyl-amine

Product 1

HCID 687361943-(6'-Methylamino-[2,2';4',3'']terpyridin-5''-yl)-phenol

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution 3-Hydroxphenolboronic acid, pinacol ester (2.0 eq, 1.172 mmol, 0.258 g) and 2M Na2CO3 (2.0 eq, 1.172 mmol, 0.586 ml) in DME (2.5 ml) is added (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-methyl-amine (Example 2.1; step1) (1 eq, 0.586 mmol, 0.200 g) followed by [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with DCM (0.1 eq, 0.059 mmol, 0.048 g). The reaction mixture is heated using microwave radiation at 90° C. for 90 mins. The reaction mixture is dissolved in DCM and washed with water. The organic layer is washed with brine, dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo. The crude residue is purified by flash chromatography (0-100% EtOAc in iso-hexane and up to 10% MeOH in EtOAc), to yield intermediate to afford the title compound; [M+H]+ 355.

Workup

  1. temperatureThe reaction mixture is heated
  2. customat 90° C.
  3. customfor 90 mins
  4. washwashed with water
  5. washThe organic layer is washed with brine
  6. customdried
  7. dry with materialover drying agent MgSO4
  8. filtrationfiltered
  9. customThe crude residue is purified by flash chromatography (0-100% EtOAc in iso-hexane
  10. customup to 10% MeOH in EtOAc), to yield intermediate

Sources & evidence

ORD record
ord-263898266d4c439b9f21add55ce3c978
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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