Nitrogen → HCID 118021971, compound

HRID 518553Notes

Reaction equation

HRID 518553 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-40ce6e1846bc4f80bdf4d07f758518a6
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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