Hydrochloric Acid → HCID 178467511, compound

HRID 991754Notes

Reaction equation

HRID 991754 reaction equation
ClC1C=C2C([CH:6]=[C:7]([C:11]3[C:12]([OH:31])=[C:13]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+]([O-])=O)[CH:23]=4)[CH:14]=[C:15]([C:17]4[NH:21][N:20]=[N:19][N:18]=4)[CH:16]=3)N2)=CC=1C(N)=N.[N+:35](C1C=C(B(O)O)C=CC=1)([O-:37])=[O:36].C([O-])([O-])=[O:48].[Na+].[Na+].Cl>C(O)C.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.C1(C)C=CC=CC=1>[OH:31][CH:12]1[C:11]([C:7](=[O:48])[CH3:6])([N+:35]([O-:37])=[O:36])[CH:16]=[C:15]([C:17]2[NH:18][N:19]=[N:20][N:21]=2)[CH:14]=[C:13]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 178511863HCID 178511863, compound

Product 1

HCID 178467511HCID 178467511, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-[3-bromo-2-hydroxy-5-(1H-tetrazol-5-yl)-phenyl]-ethanone (1, 1.07 g, 3.78 mmoles) and 3-nitrophenylboronic acid (0.69 g, 5.67 mmoles) in ethanol (8 mL) was mixes with toluene (25 mL), 2M Na2CO3 (2.8 mL) and the resulting mixture flushed with nitrogen. The nitrogen flushed reaction mixture then was combined with Pd(PPh3)4 (0.44 g, 0.38 mmoles) and the resulting solution was refluxed from about 8 to about 16 hours. The reaction mixture then was cooled to ambient temperature, acidified with 1N HCl and extracted with EtOAc (2×150 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to afford compound 2 product as a colorless oil (1.22, 100%). MS (ESI, M++1): Calc. 325.08; Found 325.9.

Workup

  1. customthe resulting mixture flushed with nitrogen
  2. customThe nitrogen flushed
  3. customreaction mixture
  4. temperaturethe resulting solution was refluxed from about 8 to about 16 hours
  5. extractionextracted with EtOAc (2×150 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cb58182e8dae4162afe3ca44d06ca6a8
Source dataset
uspto-grants-2002_10
Patent number
US06465503B2

Reaction notes

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