Potassium Carbonate → HCID 60197495, compound

HRID 878032Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[O:26]([C:28]1[N:29]=[N:30][C:31]([O:37][CH3:38])=[CH:32][C:33]=1B(O)O)[CH3:27].C([O-])([O-])=O.[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>CN(C=O)C.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>[CH3:27][O:26][C:28]1[N:29]=[N:30][C:31]([O:37][CH3:38])=[CH:32][C:33]=1[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 25, intermediate a) (200 mg, 0.468 mmol), 3,6-dimethoxylpyridazine-4-boronic acid (129 mg, 0.702 mmol, CAS RN 1015480-87-1) and K2CO3 (194 mg, 1.404 mmol) in DMF (6 mL) in a sealed tube was degassed with argon for 30 minutes. To this mixture were added S-PHOS (96 mg, 0.234 mmol, CAS RN 657408-07-6) and Pd(PPh3)4 (44 mg, 0.046 mmol), degassed for another 15 minutes, and heated to 90° C. for 1 h in microwave. Work up and purification as described in example 25 yielded 15 mg of the title compound. Off-white solid (7%). MS (ESI): m/z=487.0 [M+H]+.

Workup

customdegassed for another 15 minutes
custompurification

Sources & evidence

ORD record: ord-b1da48eaa81b464e8be236311328f409
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987307B2

Reaction notes

Loading…