HCID 48945915, compound → HCID 58625166, compound

HRID 390230Notes

Reaction equation

HRID 390230 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2].Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32]>COCCOC.C([O-])([O-])=O.[Na+].[Na+]>[CH:6]([C:5]1[CH:8]=[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:28][CH2:29][NH:30][S:31]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)(=[O:32])=[O:33])[CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])=[O:7]

Participants

5

Reactant 2

HCID 48945915HCID 48945915, compoundHCID 586251543-ForMyl-4-nitrophenyl boronicacid pinacol ester

Product 1

HCID 58625166HCID 58625166, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (0.001 mol), N-[2-(2-bromo-phenyl)-ethyl]-benzenesulfonamide (0.0012 mol) and Pd(PCy3)2Cl2 (0.00005 mol) in DME (5 mL) and 1M Na2CO3 (2 mL) in a reaction vial was stirred for 3 hours at 80° C., then DME was removed under a stream of N2 and the resulting mixture was extracted with CH2Cl2. The mixture was filtered through Extrelut, and the organic layer was blown dry, then the desired product was isolated by FAST-synthesis to yield the title compound as a residue.

Workup

  1. customDME was removed under a stream of N2
  2. extractionthe resulting mixture was extracted with CH2Cl2
  3. filtrationThe mixture was filtered through Extrelut
  4. customthe organic layer was blown dry

Sources & evidence

ORD record
ord-03e777bcb5b2470481cd460c2a6edc86
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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