Triethylamine → HCID 59305359, compound

HRID 2240968Notes

Reaction equation

HRID 2240968 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[CH:3][CH:2]=1.[CH:15]([Si:18]([C:25]#[CH:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16].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>[C:4]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:26]#[C:25][Si:18]([CH:15]([CH3:17])[CH3:16])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH:9]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734682(Triisopropylsilyl)acetyleneHCID 149586063-Bromo-N-phenylaniline

Product 1

HCID 59305359HCID 59305359, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

Into two Biotage microwave process vials (0.5-2.0 ml) were divided 3-Bromodiphenylamine (636 mg, 2.56 mmol), triisopropylsilylacetylene (0.46 g, 2.56 mmol), copper iodide (20 mg, 0.356 mmol), tetrakis(triphenylphosphine)palladium (60 mg, 0.176 mmol) and triethylamine (3.40 g, 3.36 mmol). The vials were quickly agitated then irradiated in a Biotage Initiator™ microwave instrument for 30 minutes at 80° C. The microwave reactions were recombined and purified by column chromatography (5% EtOAc/hexanes) to afford an oil 698 mg (78%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 21H) 6.82-6.86 (m, 2H) 7.00-7.12 (m, 4H) 7.15-7.28 (m, 3H) 8.23 (s, 1H); MS (ES) m/z 350.2 [M+H]+

Workup

  1. customthen irradiated in a Biotage Initiator™ microwave instrument for 30 minutes at 80° C
  2. custompurified by column chromatography (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c7cae62c8354475abc5139b7d491349e
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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