Water → Methyl 5-bromo-2'-cyano-4'-methylbiphenyl-3-carboxylate

HRID 2278724ノート

反応式

HRID 2278724 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](I)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][C:14]1[CH:15]=[CH:16][C:17](B2OC(C)(C)C(C)(C)O2)=[C:18]([CH:21]=1)[C:19]#[N:20].C(=O)([O-])[O-].[Cs+].[Cs+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[C:10]([C:17]2[CH:16]=[CH:15][C:14]([CH3:13])=[CH:21][C:18]=2[C:19]#[N:20])[CH:11]=1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 21942573Methyl 3-bromo-5-iodobenzoateHCID 584073295-Methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

生成物 1

HCID 58449349Methyl 5-bromo-2'-cyano-4'-methylbiphenyl-3-carboxylate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

Into a microwave vial were charged methyl 3-bromo-5-iodobenzoate (1.3 g, 3.8 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.1 g, 4.6 mmol), cesium carbonate (3.1 g, 9.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (44q mg, 0.38 mmol), water (3 mL) and toluene (8 mL). The reaction mixture was subjected to microwave irradiation at 100° C. for 1 h. After cooling, the reaction was filtered and concentrated. The residue was purified by reversed phase HPLC (acetonitrile:water gradient) to the title compound as a white solid. LC-MS: 331.1 [M+1]+; 1H NMR (400 MHz, CDCl3): 8.16 (s, 1H), 8.03 (t, J=1.3 Hz, 1H), 7.76 (t, J=1.8 Hz, 1H), 7.53 (s, 1H), 7.33 (dd, J=1.6, 9.4 Hz, 1H), 7.25 (d, J=8.1 Hz, 1H), 3.93 (s, 3H), 2.43 (s, 3H).

後処理

  1. customirradiation at 100° C. for 1 h
  2. temperatureAfter cooling
  3. filtrationthe reaction was filtered
  4. concentrationconcentrated
  5. customThe residue was purified by reversed phase HPLC (acetonitrile:water gradient) to the title compound as a white solid

出典と根拠

ORDレコード
ord-0099a99d653d45aea48294676221eca5
出典データセット
uspto-grants-2015_09
特許番号
US09133122B2

反応ノート

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