Triethylamine → HCID 59305334, 화합물

HRID 2240969노트

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HRID 2240969 반응식
[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

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27370071-Bromo-4-(difluoromethoxy)benzeneHCID 59305359HCID 59305359, 화합물

생성물 1

HCID 59305334HCID 59305334, 화합물수율 54.2%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-aea3a1839e864970b1dcf3e6b5ca7691
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723368B2

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