Methanol → HCID 69078191, compound

HRID 2377377Notes

Reaction equation

HRID 2377377 reaction equation
[CH:1]1([N:4]([CH3:28])[CH:5]2[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]3[CH:10]=[C:9]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=4)=[O:19])[CH:8]=[CH:7][C:6]2=3)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)[CH:60]=[O:61].[CH3:63][OH:64]>CCCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:63][O:64][C:60](=[O:61])[C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18]([NH:17][C:9]2[CH:8]=[CH:7][C:6]3[CH:5]([N:4]([CH:1]4[CH2:3][CH2:2]4)[CH3:28])[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]=3[CH:10]=2)=[O:19])=[CH:22][CH:23]=1

Participants

9

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 21107117HCID 21107117, compound2×

Product 1

HCID 69078191HCID 69078191, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure E and using 1-[5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]-3-(4-iodo-phenyl)-urea (Intermediate 58, 0.13 g, 0.267 mmol), palladium acetate (0.02 g, 0.09 mmol), 1,3-bis(diphenylphosphino)propane (0.042 g, 0.101 mmol), N,N-dimethylformamide (3 mL), methanol (3 mL) and triethyl amine (1 mL) followed by flash column chromatography over silica gel (230-400 mesh) using 30-40% ethyl acetate in hexane as the eluent the title compound was obtained (0.045 g, 40%).

Sources & evidence

ORD record
ord-d93a94d98c18464cad9a27450f1921f9
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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