Potassium Carbonate → HCID 9969788, compound

HRID 2179994Notes

Reaction equation

Cl[C:2]1[C:7]([CH2:8][CH3:9])=[N:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])=[C:4]([CH2:20][CH3:21])[N:3]=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>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>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[C:5]1[C:4]([CH2:20][CH3:21])=[N:3][C:2]([C:24]2[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:23]=2[CH3:22])=[C:7]([CH2:8][CH3:9])[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The product from step 3 (90 mg, 0.3 mmol), 2,5-dimethylphenylboronic acid (105 g, 1 mmol), tetrakis(triphenylphosphine)palladium(0) (50 mg), toluene (4 mL) and potassium carbonate (2M, 2 mL) were combined in a pressure tube and heated at 80° C. (oil bath temperature) for 16 hours. After cooling to room temperature, the upper layer is loaded onto a preparative thin layer chromatography plate and the desired product is obtained after elution with 20% ethyl acetate in hexanes. MS: 377. H-1 NMR (400 MHz, CDCl3): 1.13 (t, 3H), 1.14 (t, 3H), 2.06 (s, 3H), 2.34 (s, 3H), 2.65 (m, 4H), 3.78 (s, 3H), 3.86 (s, 3H), 6.56 (d, 1H), 6.62 (dd, 1H), 7.1-7.2 (m, 3H), 7.31 (d, 1H).

Workup

temperatureAfter cooling to room temperature

Sources & evidence

ORD record: ord-ecaad3eafe644fd5b7e61e4f2a26c8db
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887875B2

Reaction notes

Loading…