Phenylboronic Acid → 4-bromo-1-(2,2-dimethylpropyl)-5-phenoxy-1H-benzotriazole

HRID 872295ノート

反応式

HRID 872295 の反応式
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:16].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 2

HCID 66827Phenylboronic AcidHCID 574249954-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

生成物 1

HCID 679549744-bromo-1-(2,2-dimethylpropyl)-5-phenoxy-1H-benzotriazole

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (1-6) (100 mg, 0.352 mmol, 1.0 equiv.), copper(II) acetate (63.9 mg, 0.352 mmol, 1.0 equiv.), phenylboronic acid (86 mg, 0.704 mmol, 2.0 equiv.) and freshly milled 4 Å molecular sieves were dried in vacuo and then suspended in anhydrous CH2Cl2 (3.5 mL) and TEA (245 μl, 1.760 mmol, 5.0 equiv.). The mixture was stirred ambient temperature for 18 hours, after which the mixture was filtered. The filtrate was concentrated in vacuo and the residue was purified via reverse phase HPLC (water/acetonitrile gradient containing 0.1% TFA) to provide 422. 1H NMR (CDCl3) δ 7.42 (1H, d, J=8.87 Hz), 7.36-7.30 (2H, m), 7.21 (1H, d, J=8.87 Hz), 7.12-7.07 (1H, m), 6.95 (2H, dd, J=7.97, 1.44 Hz), 4.40 (2H, s), 1.06 (9H, s) ppm. LRMS m/z (M+H) 360.0 and 362.0 (intensity ratio ˜1:1) found, 360.1 and 362.1 required.

後処理

  1. filtrationafter which the mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified via reverse phase HPLC (water/acetonitrile gradient containing 0.1% TFA)

出典と根拠

ORDレコード
ord-4b7d9bfc7c92402da28a606ccba46ff3
出典データセット
uspto-grants-2015_03
特許番号
US08975286B2

反応ノート

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