Triethylamine → Tert-butyl 3-(6-(5-cyclopentylbenzofuran-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

HRID 2075153Notes

Reaction equation

HRID 2075153 reaction equation
[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12](B(O)O)=[CH:11][C:10]=3[CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)S(O[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH2:30][N:29]([CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:28][CH2:27]2)(=O)=O.C(N(CC)CC)C>C(O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([C:24]4[CH:25]=[C:26]5[C:31](=[CH:32][CH:33]=4)[CH2:30][N:29]([CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:28][CH2:27]5)=[CH:11][C:10]=3[CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59595848HCID 59595848, compoundHCID 59595895HCID 59595895, compound

Product 1

HCID 59595930Tert-butyl 3-(6-(5-cyclopentylbenzofuran-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoateYield 34%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-cyclopentylbenzofuran-2-ylboronic acid (78 mg, 0.34 mmol), tert-butyl 3-(6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate (93 mg, 0.23 mmol), triethylamine (0.95 mL, 6.8 mmol) and bis(triphenylphosphine) palladium(II) chloride (16 mg, 0.02 mmol) in ethanol (5 mL) was irradiated in a microwave instrument at 100° C. for 20 min. The reaction mixture was cooled, and the solvent was removed. The residue was purification by silica gel chromatography on ISCO system yielding the title compound (34 mg, 34% yield). 1H NMR (400 MHz, CDCl3) δ 7.59 (m, 2H), 7.40 (d, 2H), 7.15 (dd, 1H), 7.07 (d, 1H), 6.91 (s, 1H), 3.70 (s, 2H), 3.08 (m, 1H), 2.96 (dd, 2H), 2.85 (dd, 2H), 2.78 (dd, 2H), 2.54 (dd, 2H), 2.11 (m, 2H), 1.84 (m, 2H), 1.68 (m, 4H), 1.46 (s, 9H). MS (ESI) m/z: Calculated: 445.26; Observed: 446.00 (M++1).

Workup

  1. customwas irradiated in a microwave instrument at 100° C. for 20 min
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed
  4. custompurification by silica gel chromatography on ISCO system

Sources & evidence

ORD record
ord-fde28cd1bb9e450ab392b71378729515
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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