Potassium Carbonate → HCID 178524233, compound

HRID 2201473Notes

Reaction equation

HRID 2201473 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:13])[C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.C[O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[N:3]=[N+:4]([O-:13])[C:5]3[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=3[N:7]=2)=[CH:20][CH:19]=1)([OH:17])=[O:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 178526296HCID 178526296, compound

Product 1

HCID 178524233HCID 178524233, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

3-chloro-7-hydroxybenzo[e][1,2,4]triazine 1-oxide (2 mmol) was mixed with 1.0 equivalent of 4-(methoxycarbonyl)phenylboronic acid and 2 equivalents of K2CO3 in 20 ml of 50% dioxane/water. A catalytic amount of Pd(PPh3)4 was added and the mixture was heated to reflux for 2 hours. The reaction was concentrated and re-dissolved in 20 ml water and 5 ml 1N NaOH was added to hydrolyze the ester. The mixture was extracted with DCM (3×10 ml). The aqueous layer was filtered and the filtrate was neutralized with 1N HCl to pH=5. The precipitate was filtered and washed with water and dried. 500 mg of product was obtained. 1H NMR (DMSO-d6 400 MHz): δ 11.38 (s, 1H), 8.44 (d, 2H), 8.15 (m, 3H), 7.67 (d, 1H), 7.60 (s, 1H). MS (ESI): m/z 284.5 [M+1]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated
  4. dissolutionre-dissolved in 20 ml water
  5. addition5 ml 1N NaOH was added
  6. extractionThe mixture was extracted with DCM (3×10 ml)
  7. filtrationThe aqueous layer was filtered
  8. filtrationThe precipitate was filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-ece4243cc8d54d3791f55d5409ebcc73
Source dataset
uspto-grants-2016_06
Patent number
US09364481B2

Reaction notes

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