Dimethylformamide → HCID 45254329, compound

HRID 335730Notes

Reaction equation

HRID 335730 reaction equation
FC(F)(F)S(O[C:7]1[CH:20]=[C:19]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15]([N:26]4[CH2:31][CH2:30][O:29][C:28]([CH3:33])([CH3:32])[CH2:27]4)=[CH:16][C:17]=3[C@@:18]32[CH2:24][O:23][C:22]([NH2:25])=[N:21]3)=[CH:9][CH:8]=1)(=O)=O.[F:36][C:37]1[C:42](B(O)O)=[CH:41][CH:40]=[CH:39][N:38]=1.CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+]>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>[CH3:32][C:28]1([CH3:33])[CH2:27][N:26]([C:15]2[CH:14]=[CH:13][C:12]3[O:11][C:10]4[C:19](=[CH:20][C:7]([C:42]5[C:37]([F:36])=[N:38][CH:39]=[CH:40][CH:41]=5)=[CH:8][CH:9]=4)[C@@:18]4([CH2:24][O:23][C:22]([NH2:25])=[N:21]4)[C:17]=3[CH:16]=2)[CH2:31][CH2:30][O:29]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 86640721HCID 86640721, compound

Product 1

HCID 45254329HCID 45254329, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A 25 mL RB flask was charged with (R)-2-amino-2′-(2,2-dimethylmorpholino)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl trifluoromethanesulfonate (270 mg, 0.526 mmol), tetrakis(triphenylphosphine)palladium(0) (60.8 mg, 0.053 mmol), 2-fluoropyridin-3-ylboronic acid (119 mg, 0.841 mmol), DMF (2629 μL) and sodium carbonate (2M solution) (789 μL, 1.577 mmol). The mixture was stirred under argon for 2 hrs at 85° C. The mixture was diluted with water (2 ml) and extracted with 10 ml of EtOAc. Organic layer was washed with water, brine, passed through plug of Celite and concentrated. The dark residue was purified by silica gel chromatography (5-70% DCM/MeOH/NH4OH in DCM) to afford (S)-2′-(2,2-dimethylmorpholino)-7′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine.

Workup

  1. extractionextracted with 10 ml of EtOAc
  2. washOrganic layer was washed with water, brine
  3. concentrationconcentrated
  4. customThe dark residue was purified by silica gel chromatography (5-70% DCM/MeOH/NH4OH in DCM)

Sources & evidence

ORD record
ord-86de4b74327c43c2ae49a3324930ede0
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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