Triethylamine → HCID 59305359、化合物

HRID 2240968ノート

反応式

HRID 2240968 の反応式
[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

参加物

6

反応物 3

HCID 8471TriethylamineHCID 2734682(Triisopropylsilyl)acetyleneHCID 149586063-Bromodiphenylamine

生成物 1

HCID 59305359HCID 59305359、化合物収率 78%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒

実験手順

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]+

後処理

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

出典と根拠

ORDレコード
ord-c7cae62c8354475abc5139b7d491349e
出典データセット
uspto-grants-2010_05
特許番号
US07723368B2

反応ノート

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