HRID1725148

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7912

Diisopropylamine

C6H15N

HCID11073648

n-boc-propargylamine

C8H13NO2

结构：Cl.Fc1cccc(Cn2ncc3cc(Nc4ncnc5ccc(I)cc45)ccc32)c1

HCID66623800

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)NCC#Cc1ccc2ncnc(Nc3ccc4c(cnn4Cc4cccc(F)c4)c3)c2c1

HCID66623769

未命名化合物

收率 89.3%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID24350

Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)

CuI

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

[1-(3-Fluoro-benzyl)-1 H-indazol-5-yl]-(6-iodo-quinazolin-4-yl)-amine hydrochloride (0.334 g, 0.628 mmol) and Prop-2-ynyl-carbamic acid tert-butyl ester (113 mg, 1.16 equiv.) is treated with i-Pr2NH (2 equiv.) in dry THF (4 ml) under N2. Pd(PPh3)4 (25 mg, 0.0356 mmol, 5.7 mol %) and solid CuI (5 mol %) are added next, and the mixture is stirred at r.t. for 3 hours. Workup: THF is removed under reduced pressure and DCM (10 ml) is added. The organic layer is washed with sat. aq. NH4Cl solution and brine, dried and concentrated. Chromatography on silica (EtOAc/hexanes) affords the desired pure product (293 mg, 89%).

WORKUP

后处理

customWorkup: THF is removed under reduced pressure and DCM (10 ml)
additionis added
washThe organic layer is washed with sat. aq. NH4Cl solution and brine
customdried
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-582069d712d04987915ad2aabe4ac702
来源数据集: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07488823B2
来源说明: uspto-grants-2009_02

反应 SMILES

Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24](I)[CH:25]=4)[N:20]=[CH:19][N:18]=3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.[C:31]([O:35][C:36](=[O:41])[NH:37][CH2:38][C:39]#[CH:40])([CH3:34])([CH3:33])[CH3:32].N(C(C)C)C(C)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:31]([O:35][C:36](=[O:41])[NH:37][CH2:38][C:39]#[C:40][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][N:18]=[C:17]2[NH:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:6][C:5]1[CH:28]=[CH:29][CH:30]=[C:3]([F:2])[CH:4]=1)[N:8]=[CH:9]2)([CH3:34])([CH3:33])[CH3:32]