Triethylamine → Phenyl 5-(3-phenoxy-1-propynyl)-3-thiophenecarboxylate

HRID 2377254노트

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HRID 2377254 반응식
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:3]=1.[CH2:16]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17]#[CH:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.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.[Cu](I)I>[O:19]([CH2:16][C:17]#[C:18][C:2]1[S:6][CH:5]=[C:4]([C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 83613(Prop-2-ynyloxy)benzeneHCID 58591683Phenyl 5-bromothiophene-3-carboxylate

생성물 1

HCID 16220355Phenyl 5-(3-phenoxy-1-propynyl)-3-thiophenecarboxylate

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A mixture of phenyl 5-bromothiophene-3-carboxylate, Example 113 (100 mg, 0.35 mmol), (prop-2-ynyloxy)benzene (93 mg, 0.71 mmol), triphenylphosphine (19 mg, 0.071 mmol), dichlorobis(triphenylphosphine)palladium(II) (12 mg, 0.018 mmol), copper iodide (1 mg, 0.006 mmol) and triethylamine (0.74 mL, 5.30 mmol) in N,N-dimethylformamide (1 mL) was stirred under nitrogen in a heavy walled process vial in a microwave synthesizer at about 120° C. for about 25 minutes. The reaction mixture was concentrated under vacuum and the residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (2:1) as the mobile phase to provide the desired product. MS (DCI-NH3): m/z 352 (M+NH4)+.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-8c1c44f128624e6d9e7e013a7fe9f2b8
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468371B2

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