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Dimethylformamide → (4-{3-[(2,3-difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclohex-3-enyl)-carbamic acid tert-butyl ester

HRID 269505
ノート
印刷プレビュー

反応式

HRID 269505 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1C=N[O:12][C:13]=1[C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)[NH:16][CH:15]=1.C[N:30]([CH:32]=[O:33])C.[C:34]([O-])([O-])=O.[Na+].[Na+].ClC1C(Cl)=CC=CC=1[C:48]1C=N[O:51][C:52]=1[C:53]1C2C(=NC=CC=2)NC=1>CS(C)=O>[C:52]([O:51][C:32](=[O:33])[NH:30][CH:26]1[CH2:25][CH2:24][C:23]([C:20]2[CH:21]=[C:22]3[C:14]([C:13](=[O:12])[CH2:9][C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=4[F:1])=[CH:15][NH:16][C:17]3=[N:18][CH:19]=2)=[CH:28][CH2:27]1)([CH3:53])([CH3:34])[CH3:48]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 1354836473-[4-(2,3-Dichloro-phenyl)-isoxazol-5-yl]-1H-pyrrolo[2, 3-b]pyridineHCID 1360665193-[4-(2,3-Difluoro-phenyl)-isoxazol-5-yl]-5-phenyl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 59832239(4-{3-[(2,3-difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclohex-3-enyl)-carbamic acid tert-butyl ester
収率 56%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

To a solution of the above boronic ester (1.0 g, 2.5 mmol), trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohex-1-enyl ester (690 mg, 2.0 mmol, prepared from (4-Oxo-cyclohexyl)-carbamic acid tert-butyl ester (Heterocycles 58 (2002) 471-504)) in a mixed solvent of DMF (15 ml) and DMSO (6 ml) was added aqueous 2.0M Na2CO3 (2 ml, 4 mmol) and PdCl2(PPh3) 2 The mixture was degassed and heated at 80° C. under Argon for 72 h, and then concentrated under high vacuum to remove DMF. The residue was suspended in aqueous NaHCO3, then filtered. The solid was purified for FC to give (4-{3-[(2,3-difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclohex-3-enyl)-carbamic acid tert-butyl ester as a white solid (530 mg) in 56% yield, LC-MS: m/e=468.4 (M+H), 466.4 (M−H). 1H-NMR (500 MHz, CDCl3) 13.41 (br.s, 1H), 9.23 (s, 1H), 8.44 (s, 1H), 8.38 (s, 1H), 7.09 (m, 3H), 6.24 (s, 1H), 4.56 (br. s, 1H), 4.32 (s, 2H), 3.90 (br.s, 1H), 2.63 (m, 3H), 2.13 (m, 2H), 1.28 (m, 1H), 1.49 (s, 9H).

後処理

  1. customwas degassed
  2. concentrationconcentrated under high vacuum
  3. customto remove DMF
  4. filtrationfiltered
  5. customThe solid was purified for FC

出典と根拠

ORDレコード
ord-0176be0e41604a36ad25c6ce128846c9
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07446199B2

反応ノート

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