Triethylamine → (E)-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenethyl)morpholine

HRID 2281791Notes

Reaction equation

HRID 2281791 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:16][C:17]1([CH3:26])[C:21]([CH3:23])([CH3:22])[O:20][B:19]([CH:24]=[CH2:25])[O:18]1.CCN(CC)CC>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[CH3:22][C:21]1([CH3:23])[C:17]([CH3:26])([CH3:16])[O:18][B:19](/[CH:24]=[CH:25]/[C:2]2[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[O:20]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 121778014-(4-Bromophenethyl)morpholine

Product 1

HCID 66734102(E)-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenethyl)morpholineYield 77%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-(4-bromophenethyl)morpholine (731 mg, 2.71 mmol) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(PtBu3)2 (14 mg, 0.027 mmol, 1 mol %). The resulting mixture was purged with argon, then capped and heated at 80° C. (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHCO3 (10 mL), H2O (10 mL), extracted with EtOAc (30 mL×2) and dried (Na2SO4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc/hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenethyl)morpholine as a white solid (714 mg, 77%). 1H NMR (400 MHz, CDCl3) δ7.42 (d, J=8.0 Hz, 2H), 7.38 (d, J=19.0 Hz, 1H), 7.19 (d, J=7.8 Hz, 2H), 6.13 (d, J=18.3 Hz, 1H), 3.75 (t, J=4.4 Hz, 4H), 2.84-2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H).

Workup

  1. customThe resulting mixture was purged with argon
  2. customcapped
  3. temperatureAfter cooling to rt
  4. customit was quenched with sat. NaHCO3 (10 mL), H2O (10 mL)
  5. extractionextracted with EtOAc (30 mL×2)
  6. dry with materialdried (Na2SO4)
  7. customAfter evaporation of the solvents
  8. customthe residue was purified by Biotage column system (EtOAc/hex gradient: 0-100%)

Sources & evidence

ORD record
ord-4c0ecfb6f5a740e5982addc9da567e16
Source dataset
uspto-grants-2015_09
Patent number
US09139563B2

Reaction notes

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