2-Amino-3-Hydroxypyridine → 2-(3-Methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[4,5-b]pyridine

HRID 7775

Reaction equation

HRID 7775 reaction equation
C[Si](OP(=O)=O)(C)C.[NH2:9][C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][N:11]=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:15]3[C:10]([N:9]=2)=[N:11][CH:12]=[CH:13][CH:14]=3)[CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

4

Reactant 3

HCID 281142-Amino-3-HydroxypyridineHCID 16133246Trimethyl(phosphooxy)silaneHCID 219565153-Methoxy-4-(pyridin-2-yl)benzoic acid

Product 1

HCID 102863382-(3-Methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[4,5-b]pyridine

Conditions

Temperature
200 °C

Procedure

To 5 mL of trimethylsilyl polyphosphate was added 2-aminopyridin-3-ol (175 mg, 1.59 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (344 mg, 1.50 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 (3×200 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give 2-(3-methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[4,5-b]pyridine as a light yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.72 (d, 1H), 8.58 (d, 1H), 8.30 (d, 1H), 8.05–7.91 (m, 4H), 7.88 (t, 1H), 7.51 (dd, 1H), 7.40 (dd, 1H), 4.02 (s, 3H); MS (ESI) 304 (M+H)+.

Workup

  1. customquenched over ice
  2. extractionThe aqueous phase was extracted with MTBE (3×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-734dde27881f45738c88ee15ff6f7b45
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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