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

HRID 1952528
ノート
印刷プレビュー

反応式

HRID 1952528 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476
HCID 178418476、化合物
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de6d16e9d9fb4e06b0ce4613e05278fa
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08404728B2

反応ノート

読み込み中…

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