Hydrochloric Acid → HCID 86055397, compound

HRID 269993Notes

Reaction equation

[Na+].Br[C:3]1[CH:4]=[C:5]([S:13]([O-:16])(=[O:15])=[O:14])[C:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:11]=2[CH:12]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[ClH:62]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[ClH:62].[C:17]1([C:3]2[CH:4]=[C:5]([S:13]([OH:16])(=[O:15])=[O:14])[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[CH:12]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Add 7-Bromo-isoquinoline-5-sulfonic acid sodium salt (17.8 g, 55.7 mmol), phenylboronic acid (10.2 g, 83.5 mmol), N)N-dimethylformamide (178 mL), 1M sodium carbonate (111 mL, 111 mmol), palladium acetate (0.125 g, 0.56 mmol) and 1,4-bis(diphenylphosphino)butane (0.285 g, 0.67 mmol) to a flask. Heat the slurry to 70° C. for 40 minutes. Cool and filter the solids from the reaction. Add 5N hydrochloric acid to the filtrate until a thick precipitate forms. Filter the precipitate and wash the filter cake with water and then with acetone. Dry the solid in a vacuum oven at 40° C. to provide the title compound as a yellow solid. 1H NMR (DMSO, 500.0 MHz): δ 9.87 (s, 1H), 9.15 (d, 1H, J=6.5 Hz), 8.79 (s, 1H), 8.70-8.75 (m, 2H), 7.87 (d, 2H, J=8.5 Hz), 7.63 (t, 2H, J=7.5 Hz), 7.54 (t, 1H, J=7.5 Hz).

Workup

temperatureCool
filtrationfilter the solids
customfrom the reaction
filtrationFilter the precipitate
washwash the filter cake with water
customDry the solid in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-fe7fecaf19704ee19921bfd4443f7115
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449477B2

Reaction notes

Loading…