Potassium Carbonate → (S)-5-(2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl)nicotinonitrile

HRID 335742Notes

Reaction equation

HRID 335742 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[N:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C:24]1[CH:25]=[C:26]2[C@@:37]3([CH2:41][O:40][C:39]([NH2:42])=[N:38]3)[C:36]3[C:31](=[N:32][CH:33]=[C:34]([C:43]#[C:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH:35]=3)[O:30][C:27]2=[CH:28][CH:29]=1)(=O)=O.O1CCOCC1>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.O>[NH2:42][C:39]1[O:40][CH2:41][C@:37]2([C:36]3[C:31](=[N:32][CH:33]=[C:34]([C:43]#[C:44][C:45]([CH3:46])([CH3:47])[CH3:48])[CH:35]=3)[O:30][C:27]3[C:26]2=[CH:25][C:24]([C:5]2[CH:6]=[N:7][CH:8]=[C:3]([CH:4]=2)[C:1]#[N:2])=[CH:29][CH:28]=3)[N:38]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 450795765-Cyanopyridine-3-boronic acidHCID 86640725(S)-2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl trifluoromethanesulfonate

Product 1

HCID 58466178(S)-5-(2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl)nicotinonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A vial charged with 5-cyanopyridin-3-ylboronic acid (0.030 g, 0.206 mmol), palladiumtetrakis (10.80 mg, 9.35 μmol), potassium carbonate (0.129 g, 0.935 mmol), and (S)-2′-amino-3-(3,3-dimethylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (0.090 g, 0.187 mmol) was treated with 1 mL of dioxane followed by 0.4 mL water. The vial was flushed with argon and was heated to 80° C. for 4 hours. The reaction mixture was diluted with EtOAc and dried over MgSO4. The organics were then concentrated, and the crude residue was purified by column chromatography yielding (S)-5-(2′-amino-3-(3,3-dimethylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl)nicotinonitrile.

Workup

  1. customThe vial was flushed with argon
  2. additionThe reaction mixture was diluted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationThe organics were then concentrated
  5. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-6a50463b5ca543ecaaec1fcada88b4bb
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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