Water → HCID 58204233, compound

HRID 1190504Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([C:15]4[N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]=[CH:18][N:19]=4)[S:8][C:7]=3[C:6]=2[N:23]=1.C([O-])(=O)C.[K+].[CH3:29][C:30]1[C:35](B(O)O)=[CH:34][CH:33]=[CH:32][N:31]=1.C(#N)C.O>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>[CH:20]([N:16]1[CH:17]=[CH:18][N:19]=[C:15]1[C:9]1[S:8][C:7]2[C:6]3[N:23]=[C:2]([C:35]4[C:30]([CH3:29])=[N:31][CH:32]=[CH:33][CH:34]=4)[CH:3]=[CH:4][C:5]=3[O:14][CH2:13][CH2:12][C:11]=2[CH:10]=1)([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 9-Chloro-2-(1-isopropyl-1H-imidazol-2-yl)-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene (63 mg, 0.18 mmol;), Potassium acetate (60.2 mg, 0.613 mmol;), 2-methylpyridine-3-boronic acid, (32.2 mg, 0.235 mmol;) and Tetrakis(triphenylphosphine)palladium(0) (28 mg, 0.024 mmol;) in Acetonitrile (2 mL, 30 mmol;) and Water (2 mL, 100 mmol;) was degassed. The reaction was heated in the microwave at 140° C. for 20 minutes. The reaction was cooled to r.t., then extract with ethyl acetate. The combined organics were concentrated and purified by reverse phase HPLC to give 304. MS: (ESI+)=403.1. 1H NMR (400 MHz, DMSO) δ 8.55-8.47 (m, 1H), 7.86 (d, J=7.7 Hz, 1H), 7.54 (d, J=8.3 Hz, 1H), 7.50-7.43 (m, 2H), 7.36 (dd, J=7.7, 4.9 Hz, 1H), 7.29 (s, 1H), 7.00 (s, 1H), 4.82 (dt, J=13.3, 6.5 Hz, 1H), 4.43 (t, J=4.6 Hz, 2H), 2.65 (s, 3H), 1.44 (d, J=6.6 Hz, 6H).

Workup

temperatureThe reaction was cooled to r.t.
extractionextract with ethyl acetate
concentrationThe combined organics were concentrated
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-8a91d0604b824044b0702b1d42bff90e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673952B2

Reaction notes

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