1,4-Dioxane → HCID 66661906, compound

HRID 2275597Notes

Reaction equation

HRID 2275597 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]([N:20]4[CH2:24][CH2:23][C@@:22]5([C:28]6[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=6[C:26](=[O:33])[O:25]5)[CH2:21]4)=[O:19])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)O1.O1CCOCC1.Br[C:42]1[CH:43]=[CH:44][C:45]([F:48])=[N:46][CH:47]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[K+]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:48][C:45]1[N:46]=[CH:47][C:42]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]([N:20]4[CH2:24][CH2:23][C@@:22]5([C:28]6[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=6[C:26](=[O:33])[O:25]5)[CH2:21]4)=[O:19])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:43][CH:44]=1

Participants

8

Reactant 5

HCID 312751,4-DioxaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 27831685-Bromo-2-fluoropyridineHCID 66661844HCID 66661844, compound

Product 1

HCID 66661906HCID 66661906, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (1R)-1′-({1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (130 mg, 0.00029 mol) in 1,4-dioxane (1 mL, 0.01 mol) were added 5-bromo-2-fluoropyridine (0.060 mL, 0.00058 mol), tris(dibenzylideneacetone)dipalladium(0) (1 mg, 0.000001 mol), tri-tert-butylphosphine (0.71 mg, 0.0000035 mol) and potassium fluoride (56 mg, 0.00096 mol). The mixture was heated at 110° C. under nitrogen for 30 minutes. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried and concentrated. The product was purified by CombiFlash using CH2Cl2/EtOAc (max.EA 30%). LC-MS: 429.2 (M+H+)

Workup

  1. washwashed with water and brine successively
  2. customdried
  3. concentrationconcentrated
  4. customThe product was purified by CombiFlash

Sources & evidence

ORD record
ord-17ad5d81fcef42d2a45b8571b3556bfe
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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