Sodium Carbonate → HCID 59471869, compound

HRID 78638

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[S:15][CH:16]=[CH:17][C:18]=3[CH3:19])=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH:20]([S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24])([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O.CN(C=O)C>[CH:20]([S:23]([C:26]1[CH:31]=[CH:30][C:29]([C:2]2[N:3]=[C:4]([C:9]3[O:10][C:11]([C:14]4[S:15][CH:16]=[CH:17][C:18]=4[CH3:19])=[N:12][N:13]=3)[C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:28][CH:27]=1)(=[O:24])=[O:25])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave vial was charged with 5-bromo-3-[5-(3-methyl-2-thienyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-amine (75 mg, 0.2218 mmol), (4-isopropylsulfonylphenyl)boronic acid (50.59 mg, 0.2218 mmol), palladium; triphenylphosphane (12.82 mg, 0.01109 mmol) and an aqueous sodium carbonate (332.7 μL of 2 M, 0.6654 mmol) solution was then added followed by DMF (1 mL) and the vial sealed. The reaction mixture was heated in the microwave at 150° C. for 30 min. After this time water was added and the resulting precipitate collected by filtration. The precipitate was passed through a palladium scavenging column eluting with MeCN and MeOH. The solvent was removed to give the product as a yellow solid (19.2 mg, 19% yield); 1H NMR (400 MHz, DMSO) d 1.20 (d, 6H), 2.69 (s, 3H), 3.48 (t, 1H), 7.23 (d, 1H), 7.92 (d, 2H), 7.98 (d, 2H), 8.36-8.34 (m, 2H) and 9.06 (s, 1H) ppm; MS (ES+) 442.0

Workup

filtrationthe resulting precipitate collected by filtration
washeluting with MeCN and MeOH
customThe solvent was removed

Sources & evidence

ORD record: ord-4bb2711cd26748c7a2464314666fca49
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841308B2

Linked notes

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