N-Methylbenzylamine → HCID 118597637, compound

HRID 63646Notes

Reaction equation

HRID 63646 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[CH3:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:23]([N:22]([CH3:21])[C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 7669N-MethylbenzylamineHCID 10796Cesium carbonateHCID 118597993HCID 118597993, compound

Product 1

HCID 118597637HCID 118597637, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl N-[(7-bromo-3,4-dihydro-2H-1-benzopyran-4-yl)methyl]carbamate (500 mg, 1.46 mmol) in toluene (10 mL) was added N-methyl-benzylamine (212 mg, 1.75 mmol), Cs2CO3 (950 mg, 2.92 mmol), BINAP (44 mg, 0.07 mmol) and Pd(OAc)2 (16 mg, 0.07 mmol). The mixture was stirred overnight at 100° C. under nitrogen. The mixture was filtered and concentrated, and the residue was purified by prep-HPLC to give 362 mg (65%) of the title compound as a colorless gum. [M+H] Calc'd for C23H30N2O3, 383. Found, 383.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-3a139725feee4ffcbe80176630a0120e
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

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