Potassium Carbonate → [5-(1,3-Benzoxazol-2-yl)-2',4'-dimethoxy-1,1'-biphenyl-2-yl]acetonitrile

HRID 7685

反応式

HRID 7685 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O.[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]#[N:31])=[C:25](Br)[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[C:23]1[CH:24]=[CH:25][C:26]([CH2:29][C:30]#[N:31])=[C:27]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])[CH:28]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343412,4-Dimethoxybenzeneboronic acidHCID 10236618[4-(1,3-Benzoxazol-2-yl)-2-bromophenyl]acetonitrile

生成物 1

HCID 10287076[5-(1,3-Benzoxazol-2-yl)-2',4'-dimethoxy-1,1'-biphenyl-2-yl]acetonitrile

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
83 °C

実験手順

A mixture of 2,4-dimethoxyphenylboronic acid (175 mg, 0.96 mmol), [4-(1,3-benzoxazol-2-yl)-2-bromophenyl]acetonitrile (example 1) (200 mg, 0.64 mmol), dichlorobis(triphenylphosphine)palladium(II) (22 mg, 0.032 mmol), triphenylphosphine (17 mg, 0.064 mmol), and potassium carbonate (177 mg, 1.3 mmol) in degassed DME/H2O (5:1, 12 mL) was heated at 83° C. for 18 h. The mixture was cooled to rt, the two layers were separated and the aqueous layer was extracted with EtOAc (3×). The organics were combined, dried over Na2SO4 and evaporated to dryness to give an orange solid. Purification of the crude by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 40 min: 0 to 20% EtOAc, 40 to 50 min: 50% EtOAc) afforded [5-(1,3-benzoxazol-2-yl)-2′,4′-dimethoxy-1,1′-biphenyl-2-yl]acetonitrile as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.26 (dd, 1H), 8.15 (s, 1H), 7.77 (m, 1H), 7.70 (d, 1H), 7.57 (m, 1H), 7.36 (m, 2H), 7.16 (d, 1H), 6.62 (dd, 1H), 6.57 (s, 1H), 3.88 (s, 3H), 3.78 (s, 3H), 3.64 (q, 2H). MS (ESI) 371 (M+H)+.

後処理

  1. temperatureThe mixture was cooled to rt
  2. customthe two layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3×)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customto give an orange solid
  7. customPurification of the crude by flash chromatography on silica gel eluting with a gradient of EtOAc

出典と根拠

ORDレコード
ord-7014225eb7f34ab1bb1c055274cb3365
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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