Toluene → HCID 67342335、化合物

HRID 2038447ノート

反応式

HRID 2038447 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)[C-]1C=CC=C1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23]([F:34])([F:33])[F:22])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 67344690HCID 67344690、化合物

生成物 1

HCID 67342335HCID 67342335、化合物収率 49.5%

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 129828017Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To title compound of Step D (0.106 g, 0.296 mmol), 2-trifluoromethylphenylboronic acid (0.084 g, 0.444 mmol), K3PO4 (0.189 g, 0.888 mmol), Pd(dba)2 (0.007 g, 0.012 mmol) and QPhos (0.004 g, 0.006 mmol) was added PhCH3 (3 mL) and the reaction was heated to 80° C. for 18 h. The reaction was cooled to rt, diluted with EtOAc, filtered through a small silica plug and concentrated. Silica gel chromatography (0-30% EtOAc in hexanes) gave 0.062 g (49%) of the title compound. MS (ESI): mass calcd. for C22H24F3NO4, 423.17; m/z found, 368.1 [M-56]+, 446.2 [M+Na]+. 1H NMR (CDCl3): 7.73 (d, J=7.8 Hz, 1H), 7.55 (t, J=7.3 Hz, 1H), 7.46 (t, J=7.6 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 6.93 (s, 2H), 6.56 (s, 1H), 4.92-4.83 (m, 1H), 4.26 (dd, J=10.5, 6.5 Hz, 2H), 4.10 (dd, J=10.5, 4.3 Hz, 2H), 3.93 (s, 3H), 1.43 (s, 9H).

後処理

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered through a small silica plug
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-fbda97f2390e479aa36fa57f6d9dae27
出典データセット
uspto-grants-2013_11
特許番号
US08575364B2

反応ノート

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