Sodium Carbonate → HCID 23156953, compound

HRID 2110111Notes

Reaction equation

HRID 2110111 reaction equation
Br[C:2]1[O:6][C:5]([C:7]2[O:8][C:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)#[N:27]>C1(C)C=CC=CC=1.CO.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:26]([C:28]1[CH:33]=[CH:32][C:31]([C:2]2[O:6][C:5]([C:7]3[O:8][C:9]([C:12]4[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=4)=[CH:10][CH:11]=3)=[CH:4][CH:3]=2)=[CH:30][CH:29]=1)#[N:27]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 23156960HCID 23156960, compound

Product 1

HCID 23156953HCID 23156953, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Method (i): Referring now to Scheme 4, to a stirred solution of 4 (1.256 g, 4 mmol), and tetrakis(triphenylphosphine)palladium (230 mg) in toluene (8 mL) under a nitrogen atmosphere was added 4 mL of a 2 M aqueous solution of Na2CO3 followed by 4-cyanophenyl boronic acid (658 mg, 4.8 mmol) in 4 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 (250 mL) and 2 M aqueous Na2CO3 (20 mL) containing 2.4 mL of concentrated ammonia. The organic layer was dried (Na2SO4), and then concentrated to dryness under reduced pressure to afford 15 in 52% yield; mp 298-299° C. (DMF). 1H NMR (DMSO-d6); δ 7.09 (d, J=3.6 Hz, 2H), 7.39 (d, J=3.6 Hz, 2H), 7.89 (d, J=8.1 Hz, 4H), 7.97 (d, J=8.1 Hz, 4H). 13C NMR; δ 151.1, 145.8, 133.3, 132.7, 123.8, 118.6, 111.4, 109.45, 109.40. MS (m/z, rel.int.); 336 (M+, 100), 307 (5), 279 (5), 206 (15), 168 (15). High resolution calcd for C22H12N2O2 ms 336.08988. Observed 336.08978. Calcd for C22H12N2O2-0.75H2O: C, 75.52; H, 3.86; N, 8.00. Found. C, 75.12; H, 3.48; N, 7.74

Workup

  1. temperaturecooled
  2. filtrationthe precipitate was filtered
  3. customThe precipitate was partitioned between methylene chloride (250 mL) and 2 M aqueous Na2CO3 (20 mL)
  4. additioncontaining 2.4 mL of concentrated ammonia
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3b5c652496c54a96b7586b2190ade31a
Source dataset
uspto-grants-2009_04
Patent number
US07517893B2

Reaction notes

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