Potassium Phosphate, Tribasic → (3S)-N,N-Dibenzyl-5-pyridin-4-ylchroman-3-amine

HRID 1099391Notes

Reaction equation

HRID 1099391 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][C@H:10]([N:17]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][O:12]2)(=O)=O.[N:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:18]([N:17]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:10]1[CH2:9][C:8]2[C:13](=[CH:14][CH:15]=[CH:16][C:7]=2[C:37]2[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=2)[O:12][CH2:11]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25053926(3S)-N,N-Dibenzyl-5-pyridin-4-ylchroman-3-amineYield 83%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (1.00 g, 2.1 mmol), pyridine-4-boronic acid (644 mg, 5.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride (256 mg, 0.3 mmol) and potassium phosphate (1.34 g, 6.3 mmol) in dioxane (15 mL) was irradiated in a microwave at 150° C. for 2.5 h. The mixture was filtered through a pad of celite and concentrated in vacuo. Purification by column chromatography, using a gradient of ethyl acetate in heptane as the eluent, gave 707 mg (83%) of the title compound: MS (ESI) m/z 407[M+H+].

Workup

  1. customwas irradiated in a microwave at 150° C. for 2.5 h
  2. filtrationThe mixture was filtered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-516d997401424230a562b329f8364251
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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