Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)- → HCID 68312991, compound

HRID 1530494Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[C:24]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O)(=[O:31])=[O:30])([CH3:27])([CH3:26])[CH3:25]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:24]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2)(=[O:31])=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 12-bromo-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (200 mg, 0.53 mmol), 2-(N-tert-butylsulfamoyl)phenylboronic acid (274 mg, 1.07 mmol), Pd(dppf)Cl2 (38.9 mg, 0.0530 mmol), and CS2CO3 (350 mg, 1.07 mmol) in 1,4-dioxane (5 mL) was heated to 100° C. for 8 h. After filtration, the filtrate was purified by reverse phase combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to afford N-tert-butyl-2-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}benzene-1-sulphonamide (250 mg, 93% yield) as white solid. LCMS (ESI) m/z: 507.2 [M+H+]

Workup

filtrationAfter filtration
customthe filtrate was purified by reverse phase combiflash
washeluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record: ord-51125eab1a2e4d2b809003612a1fc560
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

Loading…