Triethylamine → HCID 59305309, compound

HRID 2240956Notes

Reaction equation

HRID 2240956 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1.[CH2:13]([O:15][C:16](=[O:29])[CH:17]=[C:18]1[CH2:21][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24](Br)[CH:23]=2)[CH2:19]1)[CH3:14].C(N(CC)CC)C>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl>[CH2:13]([O:15][C:16](=[O:29])[CH:17]=[C:18]1[CH2:21][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:11]#[C:10][C:7]3[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:12])[F:1])=[CH:5][CH:6]=3)[CH:23]=2)[CH2:19]1)[CH3:14]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27784971-(Difluoromethoxy)-4-ethynylbenzeneHCID 59790338Ethyl 2-[3-(3-bromophenyl)cyclobutylidene]acetate

Product 1

HCID 59305309HCID 59305309, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In a CEM snap top microwave vial were combined 1-Difluoromethoxy-4-ethynyl-benzene (1.48 g, 8.80 mmol), [3-(3-Bromo-phenyl)-cyclobutylidene]-acetic acid ethyl ester (2.00 g, 6.78 mmol), Copper iodide (232 mg, 0.131 mmol), Tetrakis(triphenylphosphine)palladium (470 mg, 1155.56 g/mol, 0.046 mmol), and triethylamine (20 g, 198 mmol). The capped vial was placed in a CEM Explorer microwave instrument and irradiated for 30 minutes at 80° C. The crude reaction mixture and dichloromethane washings were poured directly onto silica gel. Purification by column chromatography (isocratic; 5% EtOAc in hexanes) afforded an oil 1.42 g (55%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (t, J=7.2 Hz, 3H) 2.94-3.03 (m, 1H) 3.06-3.16 (m, 1H) 3.19-3.28 (m, 1H) 3.49-3.60 (m, 1H) 3.62-3.72 (m, 1H) 4.08 (q, J=7.2 Hz, 2H) 5.68-5.78 (m, 1H) 7.06-7.32 (m, 3H) 7.39 (dd, J=8.8, 3.7 Hz, 3H) 7.46-7.52 (m, 1H) 7.62 (d, J=8.8 Hz, 2H); MS (ES) m/z 383.1 [M+H]+.

Workup

  1. customirradiated for 30 minutes at 80° C
  2. additionwere poured directly onto silica gel
  3. customPurification by column chromatography (isocratic; 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-423c2e8859f34d44a85bf51b8cbb49a6
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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