HRID1482077

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

反应SMILES：COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1

HCID11269872

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

C26H35O2P

HCID23679353

Potassium ethenyl(trifluoro)borate(1-)

C2H3BF3K

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

HCID118316311

未命名化合物

PRODUCTS

产物

反应SMILES：C=Cc1c(C)c([C@H](OC(C)(C)C)C(=O)OC)c2n3cc(nc13)-c1cccc(c1)-c1cc(F)ccc1O[C@@H](C)CCCCOC1(C)CCN2CC1

HCID118316325

未命名化合物

收率 465.3%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

溶剂HCID962

Water

H2O

溶剂HCID6228

Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

Methyl(2S)-2-[(22S)-5-bromo-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]-2-(tert-butoxy)acetate (40 mg, 0.054 mmol, 1.0 equiv), potassium trifluoro(vinyl)borate (36.4 mg, 0.271 mmol, 5 equiv) were mixed in DMF (1.0 mL) and water (0.10 mL). To this solution was added Pd(OAc)2 (1.21 mg, 0.005 mmol, 0.1 equiv), Sphos (4.46 mg, 0.011 mmol, 0.2 equiv) and cesium carbonate (35.4 mg, 0.11 mmol, 2.0 equiv). The solution was degassed by N2 for five minutes. Then it was stirred at 80° C. for 2 hours. The mixture was loaded onto 12 g ISCO column and purified by 0-100% Ethyl Acetate [2% TEA]/Hexane to provide the product (35 mg, 94.3%) as a brown oil. LCMS (ESI, M+1): 684.4.

WORKUP

后处理

customThe solution was degassed by N2 for five minutes
custompurified by 0-100% Ethyl Acetate [2% TEA]/Hexane

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-6a39cd0627a949f0983efb79b7d0796d
来源数据集: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US09409922B2
来源说明: uspto-grants-2016_08

反应SMILES

Br[C:2]1[C:31]2=[N:32][C:28]3=[CH:29][N:30]2[C:5]([N:6]2[CH2:37][CH2:36]C(C)([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([CH3:35])[O:16][C:17]4[CH:18]=[CH:19][C:20]([F:34])=[CH:21][C:22]=4[C:23]4[CH:33]=[C:27]3[CH:26]=[CH:25][CH:24]=4)[CH2:8][CH2:7]2)=[C:4]([C@H:39]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[C:40]([O:42][CH3:43])=[O:41])[C:3]=1[CH3:49].[B-](F)(F)(F)[CH:51]=[CH2:52].[K+].CO[C:59]1C=CC=C(OC)[C:64]=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:45]([O:44][C@@H:39]([C:4]1[C:3]([CH3:49])=[C:2]([CH:59]=[CH2:64])[C:31]2=[N:32][C:28]3=[CH:29][N:30]2[C:5]=1[N:6]1[CH2:7][CH2:8][C:51]([CH3:52])([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([CH3:35])[O:16][C:17]2[CH:18]=[CH:19][C:20]([F:34])=[CH:21][C:22]=2[C:23]2[CH:33]=[C:27]3[CH:26]=[CH:25][CH:24]=2)[CH2:36][CH2:37]1)[C:40]([O:42][CH3:43])=[O:41])([CH3:48])([CH3:46])[CH3:47]