Water → (3S)-N,N-dibenzyl-5-pyridin-3-ylchroman-3-amine

HRID 1099392Notes

Reaction equation

HRID 1099392 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.CCCC[Sn]([C:47]1[CH:52]=[CH:51][CH:50]=[N:49][CH:48]=1)(CCCC)CCCC.O>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[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:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=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 962WaterHCID 34838483-(Tributylstannyl)pyridineHCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 25114037(3S)-N,N-dibenzyl-5-pyridin-3-ylchroman-3-amineYield 74%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

Palladium-tetrakis(triphenylphosphine) (48 mg, 0.042 mmol) and (3S)-3-(dibenzylamino) -3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (200 mg, 0.42 mmol) in dioxane (4 mL) were added to 3-(tri-N-butylstannyl)pyridine (232 mg, 0.63 mmol) under an atmosphere of argon and the resulting reaction mixture was irradiated in a microwave at 120-140° C. for 1.5 h. More palladium-tetrakis(triphenylphosphine) (48 mg, 0.042 mmol) was added and the irradiation was continued at 140° C. for 1 h. Water (20 mL) was added and the mixture was extracted with ethyl acetate. The organic phases was dried over sodium sulfate, the solvent was evaporated in vacuo and the residue purified by column chromatography, using a gradient of ethyl acetate in heptanes as the eluent, gave 63 mg (74%) of the title compound: MS (ES) m/z 407[M+H+].

Workup

  1. customthe resulting reaction mixture
  2. customwas irradiated in a microwave at 120-140° C. for 1.5 h
  3. customthe irradiation
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic phases was dried over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-bd2c6896d6b046439ec83e81398207ba
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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