Nitrogen → HCID 86700717, compound

HRID 572480Notes

Reaction equation

HRID 572480 reaction equation
Br[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[O:4][C:3]=1[C@H:13]([OH:33])[CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[CH3:41].N#N.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.CCOC(C)=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>[Si:16]([O:15][CH2:14][C@H:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:7]([C:2]=1[C:37]1[CH:38]=[CH:39][C:40]([CH3:41])=[C:35]([CH3:34])[CH:36]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)[OH:33])([C:29]([CH3:30])([CH3:31])[CH3:32])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343483,4-Dimethylphenylboronic acidHCID 68294919HCID 68294919, compound

Product 1

HCID 86700717HCID 86700717, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromo-3-((1R)-2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-1-hydroxyethyl)-1H-2-benzopyran-1-one (142 mg, 0.271 mmol) and 3,4-dimethylphenylboronic acid (61.0 mg, 0.407 mmol) in N,N-Dimethylformamide (DMF) (2.5 mL) was degassed with N2 for 10 min. The reaction mixture was treated with 2M Na2CO3 (149 μl, 0.298 mmol) and Pd(PPh3)4 (16 mg, 0.014 mmol) and irradiated in the microwave for 20 min at 120° C. The reaction mixture was diluted with EtOAc, and washed with saturated aqueous NH4Cl, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-30%) to afford the title compound (92 mg, 0.168 mmol, 62% yield) as a white solid: Rt=1.31, 1.33 (atropisomers), ES+ MS: 571 (M+23).

Workup

  1. customirradiated in the microwave for 20 min at 120° C
  2. washwashed with saturated aqueous NH4Cl, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-30%)

Sources & evidence

ORD record
ord-73385b61a6f841aebf7c2ec077c97425
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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