Water → HCID 58466260, compound

HRID 335973Notes

Reaction equation

HRID 335973 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:12]1[CH:13]=[C:14]2[C@@:26]3([CH2:30][O:29][C:28]([NH2:31])=[N:27]3)[C:25]3[C:20](=[N:21][CH:22]=[C:23]([CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:24]=3)[O:19][C:15]2=[CH:16][C:17]=1[F:18].C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.CCOC(C)=O>[C:34]([O:33][CH2:32][C:23]1[CH:24]=[C:25]2[C@:26]3([CH2:30][O:29][C:28]([NH2:31])=[N:27]3)[C:14]3[C:15](=[CH:16][C:17]([F:18])=[C:12]([C:7]4[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=4)[CH:13]=3)[O:19][C:20]2=[N:21][CH:22]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 67383534HCID 67383534, compound

Product 1

HCID 58466260HCID 58466260, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of pd(Ph3P)4 (0.019 g, 0.017 mmol), 2-fluoropyridin-3-ylboronic acid (0.047 g, 0.34 mmol), (S)-7-bromo-3-(tert-butoxymethyl)-8-fluoro-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.073 g, 0.17 mmol), and potassium carbonate (0.12 g, 0.84 mmol) in 1 mL dioxane, was treated with 0.4 mL water and was heated to 100° C. overnight. The reaction mixture was diluted with EtOAc, dried over MgSO4, and concentrated. Purification of the crude residue by column chromatography [0-100% (9:1 DCM:MeOH)/DCM] gave (4′S)-3-(tert-butoxymethyl)-8-fluoro-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.032 g, 0.071 mmol, 42.3% yield). [M+H]+=453.0

Workup

  1. dry with materialdried over MgSO4
  2. concentrationconcentrated
  3. customPurification of the crude residue by column chromatography [0-100% (9:1 DCM:MeOH)/DCM]

Sources & evidence

ORD record
ord-92e82daa4f2749ceb5de7824bb9d2112
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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