HCID 86693013, compound → HCID 86693014, compound

HRID 2173295Notes

Reaction equation

HRID 2173295 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1>CO.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>[CH3:21][O:20][C:18]([C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:19]

Participants

4

Reactant 1

HCID 86693013HCID 86693013, compound

Product 1

HCID 86693014HCID 86693014, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 4-[(7-bromo-1-benzofuran-3-yl)methyl]piperazine-1-carboxylate (100 mg, 0.253 mmol), Pd(PPh3)2Cl2 (10 mg, 0.0142 mmol) and TEA (2 mL) in 20 mL of MeOH was heated at 100° C. under CO (3 MPa) overnight. After cooling, the mixture was filtered. The filtrate was then partitioned between EtOAc and water. The combined organics were washed with water (150 mL) and brine (150 mL), dried over Na2SO4 and concentrated to give tert-butyl 4-{[7-(methoxycarbonyl)-1-benzofuran-3-yl]methyl}piperazine-1-carboxylate. 1H-NMR (400 MHz, CDCL3) δ ppm 7.88-7.91 (m, 2H), 7.59 (s, 1H), 7.24 (t, J=7.6 Hz, 1H), 3.94 (s, 3H), 3.59 (s, 2H), 3.30-3.50 (m, 4H), 2.30-2.40 (m, 4H), 1.39 (s, 9H); MS m/z 375 (M+1)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customThe filtrate was then partitioned between EtOAc and water
  4. washThe combined organics were washed with water (150 mL) and brine (150 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3b29281477b248b6ae75620fb1c93df3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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