Potassium Acetate → HCID 131733884, compound

HRID 708925Notes

Reaction equation

HRID 708925 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]3[CH2:38][CH2:37][O:36][CH2:35]3)=[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]1[CH2:38][CH2:37][O:36][CH2:35]1)[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 118092937HCID 118092937, compound

Product 1

HCID 131733884HCID 131733884, compoundYield 70.2%

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 38D (258 mg, 0.410 mmol), 5,5,5′,5′-tetramethyl-2,2′-bi(1,3,2-dioxaborinane) (111 mg, 0.492 mmol), KOAc (101 mg, 1.025 mmol) and Pd(dppf)Cl2 (67.4 mg, 0.082 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 H2O, and extracted with EtOAc (3×). The combined organic layers was filtered though silica gel and concentrated. The residue was purified by prep HPLC to give 38E (171 mg, 0.288 mmol, 70.2% yield) as a tan solid. MS (ESI) m/z: 595.4 (M+H)+.

Workup

  1. additionThe tube was filled with Ar
  2. customsealed
  3. customThe mixture was quenched with H2O
  4. extractionextracted with EtOAc (3×)
  5. filtrationThe combined organic layers was filtered though silica gel
  6. concentrationconcentrated
  7. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-5a59aca272cf4d8ea6a9ebf3bda19c7c
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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