Potassium Phosphate, Tribasic → (S)-3,7-di(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

HRID 335708

Reaction equation

HRID 335708 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12](Cl)[N:11]=[CH:10][C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C[CH:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37]C=CC=1.OP(O)(O)=O.[N:45]1[CH:50]=[CH:49][CH:48]=[C:47](B(O)O)[CH:46]=1>O1CCOCC1.O>[N:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:12]2[N:11]=[CH:10][C:9]3[O:8][C:5]4[C:4]([C@@:15]5([CH2:19][O:18][C:17]([NH2:20])=[N:16]5)[C:14]=3[CH:13]=2)=[CH:3][C:2]([C:38]2[CH:37]=[N:39][CH:31]=[CH:32][CH:33]=2)=[CH:7][CH:6]=4)[CH:46]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 27343783-Pyridinylboronic acidHCID 58466134(S)-7-bromo-3-chloro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Product 1

HCID 58466285(S)-3,7-di(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with (S)-7-bromo-3-chloro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (32 mg, 0.087 mmol), potassium phosphate (55.6 mg, 0.262 mmol), Amphos (1.525 mg, 2.153 μmol) and 3-pyridylboronic acid (32.2 mg, 0.262 mmol) in dioxane (0.6 mL) and water (0.200 mL). The reaction mixture was stirred and heated in a microwave at 100° C. for 30 min. The reaction mixture was diluted with water (mL) and extracted with EtOAc (2×5 mL). The organic extract was washed with saturated NH4Cl (2×5 mL) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude material as a yellow solid. The crude material was absorbed onto a plug of silica gel and purified by silica gel chromatography (0-10% MeOH in DCM) to provide (S)-3,7-di(pyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as white solid.

Workup

  1. customA glass microwave reaction vessel
  2. extractionextracted with EtOAc (2×5 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NH4Cl (2×5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material as a yellow solid
  9. customThe crude material was absorbed onto a plug of silica gel
  10. custompurified by silica gel chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-dded776655274b719acb40dfe7852e3c
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Linked notes

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