Triethylamine → HCID 59305334、化合物

HRID 2240969ノート

反応式

HRID 2240969 の反応式
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][Si](C(C)C)(C(C)C)C(C)C)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[C:45]1[CH:50]=[CH:49][C:48]([O:51][CH:52]([F:54])[F:53])=[CH:47][CH:46]=1.C(N(CC)CC)C>C1COCC1.[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>[NH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH:52]([F:54])[F:53])=[CH:47][CH:46]=2)[CH:9]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27370071-Bromo-4-(difluoromethoxy)benzeneHCID 59305359HCID 59305359、化合物

生成物 1

HCID 59305334HCID 59305334、化合物収率 54.2%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Phenyl-{3-[(triisopropylsilanyl)-ethynyl]-phenyl}-amine (441 mg, 1.26 mmol) was dissolved in THF (2 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (2 ml) at room temperature. The crude product (250 mg, 1.29 mmol) obtained from aqueous work-up was introduced to a Biotage microwave process vial (0.5-2.0 ml) and combined with 1-Bromo-4-Difluoromethoxybenzene (700 mg, 3.13 mmol), copper iodide (40 mg, 0.210 mmol), tetrakis(triphenylphosphine)palladium (80 mg, 0.069 mmol) and triethylamine (2.74 g, 27 mmol). The vial was quickly crimp capped, agitated then irradiated in a Biotage Initiator™ microwave instrument for 30 minutes at 80° C. Purification by column chromatography (gradient; 0-10% EtOAc in hexanes) afforded an oil 229 mg (53%). This material was used in the subsequent oxidation without further characterization.

後処理

  1. customThe crude product (250 mg, 1.29 mmol) obtained from aqueous work-up
  2. additionwas introduced to a Biotage microwave process vial (0.5-2.0 ml)
  3. customthen irradiated in a Biotage Initiator™ microwave instrument for 30 minutes at 80° C
  4. customPurification by column chromatography (gradient; 0-10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-aea3a1839e864970b1dcf3e6b5ca7691
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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