1,2-Dimethoxyethane → HCID 86602871, compound

HRID 508533Notes

Reaction equation

HRID 508533 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1B(O)[OH:10].[CH3:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16].CO[CH2:21][CH2:22][O:23][CH3:24]>>[CH2:13]([NH:14][C:24](=[O:23])[O-:10])[CH3:12].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:2]1[CH:3]=[CH:4][C:5]2[CH:21]([CH3:22])[CH:16]3[CH2:15][NH:14][CH2:17][CH:18]3[C:6]=2[CH:7]=1

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 27343362,6-Difluorophenylboronic acid

Product 1

HCID 86602871HCID 86602871, compound

Conditions

Temperature
90 °C

Procedure

2,6-Difluorophenylboronic acid (41 mg, 0.26 mmol), Pd(dppf) (5 mg), and Et3N (0.2 mL) were added to a solution of N-ethylcarbamate-5-triflate-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (52 mg, 0.13 mmol) in DME (2.6 mL), and stirred overnight at 90° C. The solution was cooled to room temperature, partitioned between CH2Cl2 and H2O, and filtered through an Extrelut column. The column was washed with CH2Cl2, and the filtrate was concentrated. The crude product was obtained without further purification. MS calculated for C21H21F2NO2+H: 358, observed: 358.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. custompartitioned between CH2Cl2 and H2O
  3. filtrationfiltered through an Extrelut column
  4. washThe column was washed with CH2Cl2
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8f3bbbcf36864af08a53c664062e2653
Source dataset
uspto-grants-2015_08
Patent number
US09096520B2

Reaction notes

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