Triethylamine → 3-Fluoro-4-(5-(piperidin-1-yl)benzofuran-2-yl)benzaldehyde

HRID 2075150Notes

Reaction equation

HRID 2075150 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13](B(O)O)=[CH:12][C:11]=3[CH:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=1[F:28].C(N(CC)CC)C>C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:28][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:20]=1[C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:18][C:11]=2[CH:12]=1)[CH:24]=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 59595903(5-(Piperidin-1-YL)benzofuran-2-YL)boronic acid

Product 1

HCID 595958383-Fluoro-4-(5-(piperidin-1-yl)benzofuran-2-yl)benzaldehydeYield 25.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(piperidin-1-yl)benzofuran-2-ylboronic acid (50 mg, 0.204 mmol), 4-bromo-3-fluorobenzaldehyde (37 mg, 0.184 mmol), triethylamine (0.56 mL, 4.1 mmol) and bis(triphenylphosphine)palladium(II) chloride (14 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 (15 mg, 15% yield). ESI-MS: 324.2 (M+H)+, 1H NMR (400 MHz, CDCl3) δ 10.00 (s, 1H), 8.19 (t, 1H), 7.75 (d, 1H), 7.67 (d, 1H), 7.43 (d, 1H), 7.35 (d, 1H), 7.14-7.11 (m, 2H), 3.13 (m, 4H), 1.77 (m, 4H), 1.59 (m, 2H).

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-bf84bc192d534eada10ad2ad348e3d5b
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

Loading…