Water → HCID 58204233, compound

HRID 708048Notes

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-ca573c3722cf4639933b960547a7d425
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175009B2

Reaction notes

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