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Triethylamine → Benzyl 4-((4-(5-bromo-4-(2-ethoxy-2-oxoethyl)thiophene-2-carbonyl)-2-nitrophenyl)ethynyl)benzoate

HRID 1952528
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HRID 1952528 반응식
[Br:1][C:2]1[S:3][C:4]([C:13](=[O:24])[C:14]2[CH:19]=[CH:18][C:17](I)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=2)=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:25]([C:27]1[CH:42]=[CH:41][C:30]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])=[CH:29][CH:28]=1)#[CH:26].C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>CN(C=O)C.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.O>[Br:1][C:2]1[S:3][C:4]([C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:26]#[C:25][C:27]3[CH:42]=[CH:41][C:30]([C:31]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:28]=3)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=2)=[O:24])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67495826Ethyl 2-(2-bromo-5-(4-iodo-3-nitrobenzoyl)thiophen-3-yl)acetateHCID 86664843Benzyl 4-ethynylbenzoate

생성물 1

HCID 67496549Benzyl 4-((4-(5-bromo-4-(2-ethoxy-2-oxoethyl)thiophene-2-carbonyl)-2-nitrophenyl)ethynyl)benzoate

시약·촉매·용매 3

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

A solution of 2 (952 mg, 1.82 mmol), benzyl 4-ethynylbenzoate (472 mg, 2.00 mmol), Pd(PPh3)2Cl2 (128 mg, 0.18 mmol), K2CO3 (250 mg, 1.81 mmol), and Et3N (238 mg, 2.36 mmol) in DMF (4 mL) was stirred for 24 hours at room temperature. Water (5 mL) was added to the mixture and then extracted with EtOAc (3×30 mL). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. MPLC purification (Hex:EtOAc/5:1) of the residue gave 3 as a solid foam (600 mg, 52%). 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 8.11-8.06 (m, 3H), 7.87 (d, J=8.0 Hz, 1H), 7.68 (d, J=8.0 Hz, 2H), 7.52 (s, 1H), 7.47-7.34 (m, 5H), 5.38 (s, 3H), 4.19 (q, J=7.2 Hz, 2H), 3.67 (s, 2H), and 1.28 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 183.86, 169.64, 165.88, 149.62, 142.04, 137.57, 136.41, 135.95, 135.92, 135.39, 133.02, 132.40, 131.08, 130.02, 129.93, 128.91, 128.66, 128.55, 126.69, 125.60, 124.44, 122.06, 99.57, 84.06, 67.32, 61.77, 35.25, and 14.42.

후처리

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customMPLC purification (Hex:EtOAc/5:1) of the residue

출처 및 근거

ORD 기록
ord-de6d16e9d9fb4e06b0ce4613e05278fa
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08404728B2

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