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1-Ethynyl-4-phenoxybenzene → HCID 178451391, 화합물

HRID 1045103
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HRID 1045103 반응식
[C:1]([O:5][C:6](=[O:20])[CH2:7][S:8][C:9]1[NH:13][C:12]2[CH:14]=[C:15]([Cl:19])[C:16](I)=[CH:17][C:11]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)#[CH:22]>CN(C=O)C.CO.CCOC(C)=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:20])[CH2:7][S:8][C:9]1[NH:13][C:12]2[CH:14]=[C:15]([Cl:19])[C:16]([C:22]#[C:21][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)=[CH:17][C:11]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

7

반응물 2

HCID 127880241-Ethynyl-4-phenoxybenzeneHCID 58387110Tert-butyl 2-(6-chloro-5-iodo-1H-benzo[d]imidazol-2-ylthio)acetate2회

생성물 1

HCID 178451391HCID 178451391, 화합물

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매
HCID 6228
Dimethylformamide
용매
2회
HCID 21584119Ethylacetate methanol용매

반응 조건

온도
120 °C

실험 절차

A 2 mL Biotage™ microwave vial equipped with a stirring bar was charged with copper iodide (1.1 mg, 10 mol %), and Pd(PPh3)2Cl2 (2.1 mg, 5 mol %). A solution of (6-chloro-5-iodo-1H-benzoimidazol-2-ylsulfanyl)-acetic acid tert-butyl ester (Intermediate 4, 25.0 mg, 0.059 mmol) in DMF (0.5 mL) was added to the vial, followed by a solution of 1-ethynyl-4-phenoxy-benzene (15.0 mg, 0.118 mmol) in DMF (250 uL) and TEA (57 uL, 0.41 mmol). The resulting suspension was heated in a microwave synthesizer (Biotage Initiator™) at 120° C. for 5 min. The solvent was removed in vacuo to give dark brown oil which was re-dissolved in a 1:1 MeOH/EtOAc mixture (3 mL) and passed through a Thiol StratoSphere™ SPE cartridge (Polymer Labs). The resulting solution was evaporated to dryness in vacuo to give the crude product as brown solid. LR-MS (API-ES): calculated for C27H23ClN2O3S 490.1, observed m/e 491.0 (M+H)+ (Rt 3.74 min). The crude product was used in the next step without further purification.

후처리

  1. customA 2 mL Biotage™ microwave vial equipped with a stirring bar
  2. customThe solvent was removed in vacuo
  3. customto give dark brown oil which
  4. customThe resulting solution was evaporated to dryness in vacuo

출처 및 근거

ORD 기록
ord-3def5c6e62b34a98af29897033c6ee11
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08563746B2

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