Cesium fluoride → 4-(6-Amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol

HRID 908446Notes

Reaction equation

HRID 908446 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[OH:18].Br[C:20]1[CH:21]=[C:22]([C:27]2[O:28][C:29]3[C:30]([N:35]=2)=[N:31][CH:32]=[CH:33][CH:34]=3)[C:23]([NH2:26])=[N:24][CH:25]=1.[F-].[Cs+]>CO.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C:7]2[CH:6]=[CH:5][C:4]([OH:18])=[C:3]([O:2][CH3:1])[CH:8]=2)=[CH:21][C:22]=1[C:27]1[O:28][C:29]2[C:30]([N:35]=1)=[N:31][CH:32]=[CH:33][CH:34]=2

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 673883775-Bromo-3-(oxazolo[4,5-b]pyridin-2-yl)pyridin-2-amine

Product 1

HCID 673884864-(6-Amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenolYield 87.1%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (90 mg), 5-bromo-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (100 mg), caesium fluoride (0.038 g) and bis(triphenylphosphine) palladium chloride (12.06 mg) were suspended in methanol (2 ml) and sealed into a microwave tube. The reaction was degassed, purged with nitrogen and heated to 120° C. over a period of 20 minutes in the microwave reactor. The solvent was removed; the residue was diluted with water (20 ml) and stirred for 30 min. The mixture was filtered, washed with water (3×10 ml), dried; and washed with diethyl ether (4×15 ml) and dichloromethane/diethyl ether (10 ml) and dried overnight to give 4-(6-amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol (100 mg); NMR Spectrum: (DMSOd6) 3.88 (s, 3H), 6.87 (d, 1H), 7.09 (dd, 1H), 7.24 (d, 1H), 7.48 (dd, 1H), 7.73 (bs, 2H), 8.25 (dd, 1H), 8.46 (d, 1H), 8.55 (dd, 1H), 8.60 (d, 1H), 9.09 (s, 1H); Mass spectrum: M+H+ 335.

Workup

  1. customsealed into a microwave tube
  2. customThe reaction was degassed
  3. custompurged with nitrogen
  4. customThe solvent was removed
  5. additionthe residue was diluted with water (20 ml)
  6. filtrationThe mixture was filtered
  7. washwashed with water (3×10 ml)
  8. customdried
  9. washand washed with diethyl ether (4×15 ml) and dichloromethane/diethyl ether (10 ml)
  10. customdried overnight

Sources & evidence

ORD record
ord-5a40ce9592cf48fc906718064596300c
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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