2-Amino-4-Bromophenol → 5-Bromo-2-(3-methoxy-4-pyridin-2-ylphenyl)-1,3-benzoxazole

HRID 7770

反応式

HRID 7770 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:15](O)=O>C[Si](OP(=O)=O)(C)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:15]([C:14]3[CH:18]=[CH:19][C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[C:12]([O:11][CH3:10])[CH:13]=3)=[N:1][C:2]=2[CH:7]=1

参加物

4

反応物 2

HCID 3518402-Amino-4-BromophenolHCID 219565153-Methoxy-4-(pyridin-2-yl)benzoic acid

生成物 1

HCID 103093885-Bromo-2-(3-methoxy-4-pyridin-2-ylphenyl)-1,3-benzoxazole

試薬・触媒・溶媒 1

HCID 16133246Trimethyl(phosphooxy)silane溶媒

反応条件

温度
200 °C

実験手順

To 20 mL trimethylsilyl polyphosphate was added 2-amino-4-bromophenol (752 mg, 4.00 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (916 mg, 4.00 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with MTBE (3×300 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (20–50% EtOAc/hexanes) to give 5-bromo-2-(3-methoxy-4-pyridin-2-ylphenyl)-1,3-benzoxazole as a pink solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.71 (d, 1H), 8.10 (d, 1H), 8.00 (t, 1H), 7.97–7.86 (m, 4H), 7.84 (d, 1H), 7.63 (dd, 1H), 7.39 (dt, (s, 3H); MS (ESI) 382 (M+H)+.

後処理

  1. customquenched over ice
  2. extractionThe aqueous phase was extracted with MTBE (3×300 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (20–50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b561074befdb46c6a83752150344d90c
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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