Potassium Carbonate → HCID 58466243, compound

HRID 1970305Notes

Reaction equation

HRID 1970305 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C@@:20]3([CH2:24][O:23][C:22]([NH2:25])=[N:21]3)[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:26]4[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=4)[CH:18]=3)[O:13][C:10]2=[CH:11][CH:12]=1)(=O)=O.[F:35][C:36]1[C:41](B(O)O)=[CH:40][CH:39]=[CH:38][N:37]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:35][C:36]1[C:41]([C:7]2[CH:8]=[C:9]3[C@@:20]4([CH2:24][O:23][C:22]([NH2:25])=[N:21]4)[C:19]4[C:14](=[N:15][CH:16]=[C:17]([C:26]5[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=5)[CH:18]=4)[O:13][C:10]3=[CH:11][CH:12]=2)=[CH:40][CH:39]=[CH:38][N:37]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 86640717HCID 86640717, compound

Product 1

HCID 58466243HCID 58466243, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A vial was charged with (S)-2′-amino-3-p-tolyl-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (45.0 mg, 0.092 mmol), 2-fluoropyridin-3-ylboronic acid (38.7 mg, 0.275 mmol), potassium carbonate (229 μL, 0.458 mmol), and Pd(PPh3)4 (5.29 mg, 4.58 μmol). The vial was flushed with Ar (g), then dioxane (458 μL) (actual amount as 1 mL) and water (0.5 mL) were added in sequence. The vial was sealed and placed in an 80° C. oil bath for 2 hours. The mixture was diluted with EtOAc, washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was chromatographed on a 12-g Redi-Sep column with 0-5% MeOH/DCM to give (S)-7-(2-fluoropyridin-3-yl)-3-p-tolyl-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (29.53 mg, 0.067 mmol, 73.6% yield) as a tan solid.

Workup

  1. customThe vial was flushed with Ar (g)
  2. additiondioxane (458 μL) (actual amount as 1 mL) and water (0.5 mL) were added in sequence
  3. customThe vial was sealed
  4. customplaced in an 80° C.
  5. customfor 2 hours
  6. additionThe mixture was diluted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was chromatographed on a 12-g Redi-Sep column with 0-5% MeOH/DCM

Sources & evidence

ORD record
ord-130a1a8d636242b0875a27b4a94fed84
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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