Diisopropylamine → HCID 57805483, compound

HRID 1037272Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[CH:21].C(NC(C)C)(C)C>O1CCOCC1.[Cu](I)I.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:22]1([C:20]#[C:21][C:2]2[CH:7]=[CH:6][C:5]([C:8]3([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of tert-butyl 1-(4-bromophenyl)cyclobutylcarbamate (1.53 g, 4.7 mmol), ethynylbenzene (2.5 mL, 22.6 mmol), copper iodide (36 mg, 0.24 mmol) and diisopropylamine (3.2 mL, 22.6 mmol) in dioxane (3 mL) was degassed for 30 min, followed by the addition of bis(tri-tert-butylphosphine)palladium (144 mg, 0.36 mmol). The resulting mixture was heated at 90° C. for 16 h, after cooled down to RT, concentrated to dryness. The crude residue was purified by column chromatography (eluting with 10% DCM in heptane) to give the title compound (0.85 g, 52%). 1H NMR (500 MHz, CDCl3): 7.58-7.54 (m, 4H), 7.48-7.43 (m, 2H), 7.39-7.20 (m, 3H), 2.55-2.40 (m, 4H), 2.15-2.10 (m, 1H), 1.93-1.84 (m, 1H), 1.45-1.20 (br s, 9H).

Workup

customwas degassed for 30 min
temperatureafter cooled down to RT
concentrationconcentrated to dryness
customThe crude residue was purified by column chromatography (eluting with 10% DCM in heptane)

Sources & evidence

ORD record: ord-370d4bf0e0984a6f9d52f6f517651497
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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