Sodium Bicarbonate → HCID 67109272, compound

HRID 2370996Notes

Reaction equation

Br[C:2]1[N:3]([C:19]#[N:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:21][C:22]1[C:26](B(O)O)=[C:25]([CH3:30])[S:24][N:23]=1.C(=O)([O-])O.[Na+]>COCCOC.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>[CH3:21][C:22]1[C:26]([C:2]2[N:3]([C:19]#[N:20])[C:4]3[C:9]([C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[C:25]([CH3:30])[S:24][N:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-bromo-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile (70.0 mg, 0.21 mmol), tetrakis(triphenylphosphine)palladium (24.7 mg, 0.21 mmol) and 3,5-dimethylisothiazol-4-ylboronic acid (102.3 mg, 0.43 mmol) were mixed in 3.5 ml DME and 0.86 ml sodium hydrogen carbonate (1 M) under nitrogen. The resulting mixture was heated at 120° C. for 20 min in microwave. The solvent was evaporated and the residue was dissolved in DCM. Filtering through a short plug of silica gave a crude product which was purified on silica (EtOAc/n-Heptane 1:4). 38.0 mg 2-(3,5-dimethylisothiazol-4-yl)-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile was obtained.

Workup

customThe solvent was evaporated
dissolutionthe residue was dissolved in DCM
filtrationFiltering through a short plug of silica
customgave a crude product which
customwas purified on silica (EtOAc/n-Heptane 1:4)

Sources & evidence

ORD record: ord-eb3647e48cb14f72a9b3b7e851370a4c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710243B2

Reaction notes

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