Binap, (A+-)- → [4-(2-Morpholin-4-yl-pyridin-4-ylamino)-naphthalen-1-yl]-oxo-acetic acid methyl ester

HRID 2353549Notes

Reaction equation

HRID 2353549 reaction equation
[N:1]1([C:7]2[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:14][O:15][C:16](=[O:30])[C:17]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](Br)=[CH:21][CH:20]=1)=[O:18].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>C1(C)C=CC=CC=1.O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][O:15][C:16](=[O:30])[C:17]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([NH:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[CH:12]=2)=[CH:21][CH:20]=1)=[O:18]

Participants

6

Reactant 3

HCID 634876Binap, (A+-)-HCID 238188102-(Morpholin-4-yl)pyridin-4-amineHCID 59379801(4-Bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester

Product 1

HCID 59379817[4-(2-Morpholin-4-yl-pyridin-4-ylamino)-naphthalen-1-yl]-oxo-acetic acid methyl esterYield 40.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateSolventHCID 21840791Dioxane tolueneSolvent

Procedure

2-Morpholin-4-yl-pyridin-4-ylamine (159 mg, 0.88 mmol) and (4-Bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester (18) (260 mg, 0.89 mmol) were suspended in 6 mL toluene/Dioxane 1/1 and Pd(OAc)2 (6 mg, 3 mol %), BINAP (27 mg, 5 mol %) and CS2CO3 (858 mg, 2.64 mmol) were added. The reaction mixture was stirred from 80° C. to 80° C. over 18 hrs. The cooled mixture was purified by column chromatography (0-100% EtOAc/Hex) to yield 140 mg of product. This product was subjected to the methods described previously to obtain the final compounds of interest.

Workup

  1. customThe cooled mixture was purified by column chromatography (0-100% EtOAc/Hex)

Sources & evidence

ORD record
ord-8f8ee788ef504c2183ba41a6e9b5eb50
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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