Water → HCID 58466137, compound

HRID 335777Notes

Reaction equation

HRID 335777 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:18]1[CH:19]=[C:20]2[C:31]3([CH2:35][O:34][C:33]([NH2:36])=[N:32]3)[C:30]3[C:25](=[N:26][CH:27]=[C:28]([O:37][CH2:38][C:39]([O:42][CH3:43])([CH3:41])[CH3:40])[CH:29]=3)[O:24][C:21]2=[CH:22][CH:23]=1.O>C1COCC1.CCOC(C)=O.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:1][C:2]1[C:7]([C:18]2[CH:19]=[C:20]3[C:31]4([CH2:35][O:34][C:33]([NH2:36])=[N:32]4)[C:30]4[C:25](=[N:26][CH:27]=[C:28]([O:37][CH2:38][C:39]([O:42][CH3:43])([CH3:40])[CH3:41])[CH:29]=4)[O:24][C:21]3=[CH:22][CH:23]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 67241370HCID 67241370, compound

Product 1

HCID 58466137HCID 58466137, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A vial charged with 2-fluoropyridin-3-ylboronic acid (0.156 g, 1.105 mmol), palladiumtetrakis (0.043 g, 0.037 mmol), potassium carbonate (0.255 g, 1.842 mmol), and 7-bromo-3-(2-methoxy-2-methylpropoxy)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.160 g, 0.368 mmol) was dissolved in 3 mL THF and 0.5 mL water and was heated to 110° C. 2 hours. The reaction mixture was diluted with EtOAc and dried over MgSO4. The organcis were concentrated then purified directly by column chromatography yielding 7-(2-fluoropyridin-3-yl)-3-(2-methoxy-2-methylpropoxy)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine.

Workup

  1. custom2 hours
  2. dry with materialdried over MgSO4
  3. concentrationThe organcis were concentrated
  4. customthen purified directly by column chromatography

Sources & evidence

ORD record
ord-75d9a18b7d64431e8bb2662fe38c5fc9
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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