Sodium Bicarbonate → HCID 10869392, compound

HRID 853805Notes

Reaction equation

HRID 853805 reaction equation
Br[C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21]>C1(C)C=CC=CC=1.CO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[O:6][C:5]([C:7]3[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=3)=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)#[N:21]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343264-Cyanophenylboronic acidHCID 10911902HCID 10911902, compound

Product 1

HCID 10869392HCID 10869392, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Continuing with Scheme 3, to a stirred solution of 15 (1.245 g, 5 mmol), and tetrakis(triphenylphosphine) palladium (288 mg) in toluene (15 mL) under a nitrogen atmosphere was added 10 mL of a 1 M aqueous solution of NaHCO3 followed by 4-cyanophenyl boronic acid (821 mg, 4.6 mmol) in 5 mL of methanol. The vigorously stirred mixture was warmed to 80° C. for 24 h, then cooled, and the precipitate was filtered. The precipitate was partitioned between methylene chloride (300 mL) and 1 M aqueous NaHCO3 (50 mL). The organic layer was dried (Na2SO4), and then concentrated to dryness under reduced pressure to afford 16 in 64% yield; mp 276–277° C. (DMF). 1H nmr(DMSO-d6); δ 7.49 (d, J=3.6 Hz, 1H), 7.59 (d, J=3.6 Hz, 1H), 7.95 (d, J=8.7 Hz, 2H), 8.10 (d, J=8.7 Hz, 2H). 8.14 (d, J=8.1 Hz 1H), 8.49 (dd, J=8.1, 1.5 Hz, 1H), 9.29 (d, J=1.5 Hz, 1H). 13C nmr; δ 153.0, 149.7, 146.3, 133.1, 132.8, 131.4, 130.4, 129.0, 128.5, 124.4, 118.6, 117.4, 113.2, 111.8, 110.0. Calcd. for C17H9N3O: C, 75.26; H, 3.34; N, 15.49. Found. C, 75.02; H, 3.35; N, 15.39.

Workup

  1. temperaturecooled
  2. filtrationthe precipitate was filtered
  3. customThe precipitate was partitioned between methylene chloride (300 mL) and 1 M aqueous NaHCO3 (50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-682ff579a222460e9eff70cd7cd42612
Source dataset
uspto-grants-2007_08
Patent number
US07256203B2

Reaction notes

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