HRID1482138

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COC(=O)[C@@H](OC(C)(C)C)c1c(C)c(Br)c2nc3c(Br)n2c1N1CCC(C)(CC1)OCCCC[C@H](C)Oc1ccc(F)cc1-c1cccc-3c1

HCID118316310

未命名化合物

HCID178514179

未命名化合物

PRODUCTS

生成物

结构：COC(=O)[C@@H](OC(C)(C)C)c1c(C)c(C#N)c2nc3cn2c1N1CCC(C)(CC1)OCCCC[C@H](C)Oc1ccc(F)cc1-c1cccc-3c1

HCID118316373

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23994

Zinc

结构：Cl[Pd]Cl.[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1

催化剂HCID178418228

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

C34H28Cl2FeP2Pd

溶剂HCID31374

Dimethylacetamide

C4H9NO

CONDITIONS

反应条件

温度: 150 °C

PROCEDURE

实验过程

Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (50 mg, 0.061 mmol, 1.0 equiv) was placed in a microwave tube, followed by zinc (0.401 mg, 6.13 μmol, 0.1 equiv), dicyanozinc (14.40 mg, 0.123 mmol, 2.0 equiv), and Pd(dppf)Cl2 (50.1 mg, 0.061 mmol, 1.0 equiv). To this mixture was added DMAC (681 μl) and degassed, sealed, placed in microwave, and stirred for 2 hours at 150° C. Then it was diluted by 10 mL EA, washed by NaHCO3, dried over MgSO4, concentrated to give the pure enough product. LCMS (ESI, M+1): 683.4.

WORKUP

后处理

customdegassed
customsealed
additionThen it was diluted by 10 mL EA
washwashed by NaHCO3
dry with materialdried over MgSO4
concentrationconcentrated
customto give the pure enough product

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8572ed4cf5724b958e4ecf9705a0bebe
来源数据集: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09409922B2
来源说明: uspto-grants-2016_08

反应 SMILES

[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39](Br)[C:38]2=[N:43][C:35]3=[C:36](Br)[N:37]2[C:12]=1[N:13]1[CH2:49][CH2:48][C:16]([CH3:50])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:47])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:46])=[CH:28][C:29]=2[C:30]2[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[C:51]([Zn]C#N)#[N:52]>[Zn].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].CC(N(C)C)=O>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([C:51]#[N:52])[C:38]2=[N:43][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:49][CH2:48][C:16]([CH3:50])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:47])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:46])=[CH:28][C:29]=2[C:30]2[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2]