Triethylamine → HCID 86677438, compound

HRID 2364952Notes

Reaction equation

HRID 2364952 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C@@H:10]3[N:16]([CH:17]=2)[C:15](=[O:18])[C:14]2[CH:19]=[C:20]([O:61][CH3:62])[C:21]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]4[C:58]([O:59][CH3:60])=[CH:57][C:31]5[C:32](=[O:56])[N:33]6[CH:48]=[C:47](S(C(F)(F)F)(=O)=O)[CH2:46][C@H:34]6[C:35](=[O:45])[N:36]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:30]=5[CH:29]=4)=[CH:22][C:13]=2[N:12]([CH2:63][O:64][CH2:65][CH2:66][Si:67]([CH3:70])([CH3:69])[CH3:68])[C:11]3=[O:71])=[CH:4][CH:3]=1.[C:72]1(/[CH:78]=[CH:79]/B(O)O)[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1.C(N(CC)CC)C>C(O)C.C1(C)C=CC=CC=1.O.ClCCl.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>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C@@H:10]3[N:16]([CH:17]=2)[C:15](=[O:18])[C:14]2[CH:19]=[C:20]([O:61][CH3:62])[C:21]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]4[C:58]([O:59][CH3:60])=[CH:57][C:31]5[C:32](=[O:56])[N:33]6[CH:48]=[C:47]([CH:79]=[CH:78][C:72]7[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=7)[CH2:46][C@H:34]6[C:35](=[O:45])[N:36]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:30]=5[CH:29]=4)=[CH:22][C:13]=2[N:12]([CH2:63][O:64][CH2:65][CH2:66][Si:67]([CH3:70])([CH3:69])[CH3:68])[C:11]3=[O:71])=[CH:4][CH:3]=1

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 5702628Styrylboronic acidHCID 86656479HCID 86656479, compound

Product 1

HCID 86677438HCID 86677438, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of triflate 9 (0.5 g), trans-2-phenylvinylboronic acid (0.091 g), triethylamine (0.38 g) and tetrakis(triphenylphosphine)palladium(0) (30 mL) in ethanol (3 mL), toluene (6 mL) and water (1 mL) was irradiated with microwaves for 8 minutes at 80° C. in a sealed microwave vial. The reaction mixture was diluted with dichloromethane washed with water and dried over magnesium sulphate. Excess solvent was removed by rotary evaporation under reduced pressure to afford the crude product which was used without further purification in the next reaction. Retention time 8.13 mins, ES+1014.13.

Workup

  1. customwas irradiated with microwaves for 8 minutes at 80° C. in a sealed microwave vial
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. customExcess solvent was removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-8d99cfbaac244660b713760e16339d34
Source dataset
uspto-grants-2014_04
Patent number
US08697688B2

Reaction notes

Loading…