Trimethyl(phosphooxy)silane → 2-(3-Methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[5,4-b]pyridine

HRID 7779

反応式

HRID 7779 の反応式
C[Si](OP(=O)=O)(C)C.[NH2:9][C:10]1[C:11]([OH:16])=[N:12][CH:13]=[CH:14][CH:15]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:22](O)=O>>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:22]2[O:16][C:11]3[C:10]([N:9]=2)=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

参加物

4

反応物 3

HCID 16133246Trimethyl(phosphooxy)silaneHCID 219565153-Methoxy-4-(pyridin-2-yl)benzoic acidHCID 178418824HCID 178418824、化合物

生成物 1

HCID 101717932-(3-Methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[5,4-b]pyridine

反応条件

温度
200 °C

実験手順

To 5 mL of trimethylsilyl polyphosphate was added 3-aminopyridin-2-ol (150 mg, 1.59 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (229 mg, 1.0 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 EtOAc (3×200 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resultant oil was taken up in a minimum of EtOAc and purified by prep TLC (1:1 EtOAc/hexanes) to give 2-(3-methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[5,4-b]pyridine as a light yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.73 (dq, 1H), 8.43 (dd, 1H), 8.32 (dd, 1H), 8.02 (d, 1H), 7.99–7.93 (m, 2H), 7.92–7.85 (m, 2H), 7.55 (dd, 1H), 7.40 (ddd, 1H), 4.01 (s, 3H); MS (ESI) 304 (M+H)+.

後処理

  1. customquenched over ice
  2. extractionThe aqueous phase was extracted with EtOAc (3×200 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 prep TLC (1:1 EtOAc/hexanes)

出典と根拠

ORDレコード
ord-be8c3b92fc5f4f4dbb28ec056f335f02
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

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