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

HRID 598717Notes

Reaction equation

HRID 598717 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-471ba277d1b44d6789569f174e2ae90c
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

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