Methanol → HCID 69848343, compound

HRID 352229Notes

Reaction equation

HRID 352229 reaction equation
I[C:2]1[C:11]2[N:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][NH:19][C:20](=[O:27])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:13]3)[C:9](=[O:28])[C:8]3=[C:29]([CH3:32])[O:30][N:31]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(#N)C.[CH3:36][OH:37].CCN(CC)CC.C[C:46](C)=[O:47].ClCCl>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]>[CH3:36][O:37][C:46]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13]1)[C:9](=[O:28])[C:8]1=[C:29]([CH3:32])[O:30][N:31]=[C:7]21)=[O:47]

Participants

7

Reactant 5

HCID 887MethanolHCID 6342AcetonitrileHCID 8471TriethylamineHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 22714005HCID 22714005, compound

Product 1

HCID 69848343HCID 69848343, compoundYield 83%

Reagents, catalysts & solvents 1

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

Procedure

In a fashion similar to that described for Example 592, N-[3-(6-Iodo-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylmethyl]-benzamide (0.048 g, 0.089 mmol), acetonitrile (10 ml), MeOH (5 ml), Et3N (0.04 ml, 0.267 mmol), and PdCl2(dppf) (0.004 g, 0.004 mmol) gave the title compound (0.035 g, 83%) after column chromatography (silica gel, acetone/dichloromethane gradient). MS(FIA) (m/z) 472.3 [M−1].

Sources & evidence

ORD record
ord-adf265608bff4364b9ef4a61fd4db503
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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