Potassium Acetate → HCID 131733880, compound

HRID 708920Notes

Reaction equation

HRID 708920 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][C@@H:34]([CH3:38])[CH2:35][O:36][CH3:37])=[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.CC([O-])=O.[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][C@@H:34]([CH3:38])[CH2:35][O:36][CH3:37])[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 118093126HCID 118093126, compound

Product 1

HCID 131733880HCID 131733880, compoundYield 68.2%

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 reaction tube was added 37C (480 mg, 0.76 mmol), 5,5,5′,5′-tetramethyl-2,2′-bi(1,3,2-dioxaborinane) (206 mg, 0.912 mmol), KOAc (186 mg, 1.900 mmol), Pd(dppf)Cl2 (125 mg, 0.152 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, and extracted with EtOAc. The combined organic layer was filtered though silica gel and concentrated. The crude product was purified by flash chromatography to give 37D (309 mg, 0.518 mmol, 68.2% yield). MS (ESI) m/z: 597.4 (M+H)+.

Workup

  1. additionThe tube was filled with Ar
  2. customsealed
  3. customThe mixture was quenched with water
  4. extractionextracted with EtOAc
  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-121eca944c684d248cbdd32780ee1dce
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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