Cesium carbonate → HCID 57959381, compound

HRID 2091447Notes

Reaction equation

HRID 2091447 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)=[O:7])=[CH:4][N:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=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>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[O:16][CH3:17])[CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:20]=[CH:21][C:2]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 57959389HCID 57959389, compound

Product 1

HCID 57959381HCID 57959381, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture consisting of 6-bromo-N-(3,4-dimethoxybenzyl)nicotinamide (1.11 g), phenylboronic acid (0.77 g), and tetrakis(triphenylphosphine)palladium(0) (0.365 g) in N,N-dimethylformamide (20 mL) under a nitrogen atmosphere was added a 2 M aqueous cesium carbonate (6 mL). The stirring mixture was heated to 90° C. for two hours and was subsequently partitioned between ethyl acetate (200 mL) and water (200 mL). The phases were separated and the organic phase was washed twice with fresh portions of water (2×200 mL) and brine solution (150 mL), was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide an orange solid. The solid was triturated with 1:1 v/v hexanes-ethyl acetate and collected by filtration to afford the title compound as a solid (0.447 g, 40.6% yield); 1H-NMR (300 MHz; CDCl3) δ 9.06 (d, 1H, J=2.1 Hz), 8.20 (dd, 1H, J=8.4, 2.4 Hz), 8.05-8.01 (m, 2H), 7.81 (dd, 1H, J=8.4, 0.6 Hz), 7.51-7.47 (m, 3H), 6.92-6.84 (m, 3H), 6.51 (broad t, 1H), 4.62 (d, 2H, J=5.7 Hz), 3.891 (s, 3H), 3.888 (s, 3H); Rf 0.17 with 7:3 v/v hexanes-ethyl acetate; MS (APCl+) m/z 349 (M+1).

Workup

  1. customwas subsequently partitioned between ethyl acetate (200 mL) and water (200 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed twice with fresh portions of water (2×200 mL) and brine solution (150 mL)
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide an orange solid
  8. customThe solid was triturated with 1:1 v/v hexanes-ethyl acetate
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2e2bf39f068747fd92d521e875040617
Source dataset
uspto-grants-2013_05
Patent number
US08440417B2

Reaction notes

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