HRID1045469

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID2760077

1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

C10H17BN2O2

结构：COC(=O)N1CC(c2nc(-c3ccc(C)c(NC(=O)c4cnc5cc(Br)ccn45)c3)no2)C1

HCID71281208

未命名化合物

PRODUCTS

生成物

结构：COC(=O)N1CC(c2nc(-c3ccc(C)c(NC(=O)c4cnc5cc(-c6ccn(C)n6)ccn45)c3)no2)C1

HCID71281003

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

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HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

Methyl 3-(3-(3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (42) (40 mg, 0.078 mmol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (19.6 mg, 0.094 mmol) and Pd(PPh3)4 (9 mg, 0.0078 mmol) were added to a flask equipped with a stir bar. The flask was evacuated and backfilled with nitrogen several times. DMF (1 mL) and 1.8 M K2CO3 (0.094 mmol) were added by syringe. The flask was sealed and heated at 80° C. for 12 hours. The reaction was filtered and directly purified by preparative reverse phase HPLC to afford methyl 3-(3-(4-methyl-3-(7-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamido)phenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F56). MS m/z 513.2 (M+1)+.

WORKUP

后处理

customequipped with a stir bar
customThe flask was evacuated
customThe flask was sealed
filtrationThe reaction was filtered
customdirectly purified by preparative reverse phase HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c39bc1778e3847e98288af192a7f9a91
来源数据集: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08569283B2
来源说明: uspto-grants-2013_10

反应 SMILES

Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([C:21]4[N:25]=[C:24]([CH:26]5[CH2:29][N:28]([C:30]([O:32][CH3:33])=[O:31])[CH2:27]5)[O:23][N:22]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:34][N:35]1[CH:39]=[CH:38][C:37](B2OC(C)(C)C(C)(C)O2)=[N:36]1.C([O-])([O-])=O.[K+].[K+]>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.CN(C=O)C>[CH3:20][C:19]1[CH:18]=[CH:17][C:16]([C:21]2[N:25]=[C:24]([CH:26]3[CH2:27][N:28]([C:30]([O:32][CH3:33])=[O:31])[CH2:29]3)[O:23][N:22]=2)=[CH:15][C:14]=1[NH:13][C:11]([C:8]1[N:5]2[CH:6]=[CH:7][C:2]([C:37]3[CH:38]=[CH:39][N:35]([CH3:34])[N:36]=3)=[CH:3][C:4]2=[N:10][CH:9]=1)=[O:12]