HRID451561

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21

HCID636044

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C39H32OP2

HCID4445035

Sodium phenolate

C6H5NaO

HCID56932105

tert-Butyl 4-amino-3,3-difluoropiperidine-1-carboxylate

C10H18F2N2O2

HCID67342605

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CCC(Nc2nc3c(-c4ccc(F)c(F)c4F)cccn3n2)C(F)(F)C1

HCID67342863

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：ClC(Cl)Cl.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID11029508

1,4-Pentadien-3-one, 1,5-diphenyl-, (1E,4E)-, compd. with trichloromethane, palladium salt (3:1:2)

C52H43Cl3O3Pd2

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 160 °C

PROCEDURE

实验过程

Through a suspension of 4-amino-3,3-difluoro-piperidine-1-carboxylic acid tert-butyl ester (90 mg, 381 μmol), 2-bromo-8-(2,3,4-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyridine (prepared in analogy to example 66a-d, 162 mg, 495 μmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (15.8 mg, 15.2 μmol), sodium phenoxide (65.2 mg, 533 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (17.6 mg, 30.5 μmol) in dry dioxane (5.0 mL) was bubbled argon for 5 minutes, then heated to 160° C. in the microwave for 60 minutes. The catalyst was filtered off, washed with CH2Cl2 and the solvents evaporated. The residue was purified by flash chromatography (silica gel, 70 g, 0% to 100% EtOAc in heptane). The title compound was obtained as orange solid (27 mg, 15%).

WORKUP

后处理

customwas bubbled argon for 5 minutes
filtrationThe catalyst was filtered off
washwashed with CH2Cl2
customthe solvents evaporated
customThe residue was purified by flash chromatography (silica gel, 70 g, 0% to 100% EtOAc in heptane)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f989cf8297714e67a8f2f76e7f45a5f3
来源数据集: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08486967B2
来源说明: uspto-grants-2013_07

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[C:10]([F:16])([F:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:18]1[N:35]=[C:21]2[C:22]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[C:27]=3[F:34])=[CH:23][CH:24]=[CH:25][N:20]2[N:19]=1.[O-]C1C=CC=CC=1.[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:18]2[N:35]=[C:21]3[C:22]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[C:27]=4[F:34])=[CH:23][CH:24]=[CH:25][N:20]3[N:19]=2)[C:10]([F:16])([F:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]