Potassium Acetate → HCID 131733877, compound

HRID 708903Notes

Reaction equation

HRID 708903 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:40])[CH2:9][O:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([F:39])[C:17]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])=[C:18]([CH:32]=2)[CH2:19][N:20]([CH3:31])[C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:12])=[C:4]([CH3:41])[CH:3]=1.CC1(C)C[O:47][B:46](B2OCC(C)(C)CO2)[O:45]C1.C([O-])(=O)C.[K+]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:23]([O:22][C:21]([N:20]([CH2:19][C:18]1[CH:32]=[C:14]([NH:13][C:11]([O:10][CH2:9][C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([B:46]([OH:47])[OH:45])=[CH:3][C:4]=2[CH3:41])[CH3:40])=[O:12])[CH:15]=[C:16]([F:39])[C:17]=1[O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH3:31])=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 131733876HCID 131733876, compound

Product 1

HCID 131733877HCID 131733877, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a tube was added 28C (373 mg, 0.591 mmol), 5,5,5′,5′-tetramethyl-2,2′-bi(1,3,2-dioxaborinane) (160 mg, 0.709 mmol), potassium acetate (145 mg, 1.477 mmol), Pd(dppf)Cl2 (97 mg, 0.118 mmol) in DMSO (1.5 ml). The tube was filled with Ar, sealed and stirred at 85° C. for 2 h. The mixture was quenched with water, extracted with EtOAc (3×20 ml). The combined organic layer was filtered though silica gel and concentrated. The crude product was purified by flash chromatography to give 28D (210 mg, 0.352 mmol, 59.6% yield). MS (ESI) m/z: 597.3 (M+H)+.

Workup

  1. additionThe tube was filled with Ar
  2. customsealed
  3. customThe mixture was quenched with water
  4. extractionextracted with EtOAc (3×20 ml)
  5. filtrationThe combined organic layer was filtered though silica gel
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-70e337889b644c62acda7feb7d039c31
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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