Nitrogen → HCID 118021971, compound

HRID 575819Notes

Reaction equation

HRID 575819 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2B2OC(C)(C)C(C)(C)O2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].N#N.[CH3:33][N:34]([CH:36]=[O:37])[CH3:35]>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]>[CH:33]1([N:34]2[CH:35]=[C:3]([C:7]3[CH:8]=[C:9]([S:12]([CH3:15])(=[O:13])=[O:14])[CH:10]=[CH:11][C:6]=3[O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH:2]=[C:1]([CH3:4])[C:36]2=[O:37])[CH2:11][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1234348592-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118021971HCID 118021971, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

The title compound of step 4 (27 mg, 0.11 mmol), the title compound of Example 90, step 1 (46 mg, 0.13 mmol), K2CO3 (46 mg, 0.33 mmol) and Pd(dppf)2Cl2 (8 mg, 0.011 mmol) in DMF (2 mL) was N2 purged and microwaved at 100° C. After 2 h, the mixture was concentrated under vacuum and DCM was added which was washed with water, brine and dried over Na2SO4. Purification by preparative TLC gave the title compound (25 mg, 58%) as a white solid.

Workup

  1. custompurged
  2. custommicrowaved at 100° C
  3. concentrationthe mixture was concentrated under vacuum and DCM
  4. additionwas added which
  5. washwas washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customPurification by preparative TLC

Sources & evidence

ORD record
ord-6ad47f9c5f41456081bfb5f1cd9249da
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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