Ethanol → HCID 86698824, compound

HRID 1054834Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][NH:8]2)=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.[C:24]([O-:27])(=[O:26])C.[Na+].[CH2:29](O)[CH3:30]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:24]([O:27][CH2:29][CH3:30])=[O:26])=[N:7][NH:8]2)=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A Parr shaker bottle was charged with 6-chloro-3-iodo-5-[4-(morpholin-4-yl)phenyl]-1H-indazole (86.6 mg, 0.197 mmol), sodium acetate (68 mg, 0.83 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (30.0 mg, 0.039 mmol), and ethanol (20 mL) and shaken under an atmosphere of carbon monoxide (40 psi) at 70° C. for 72 hours. The reaction was cooled and the pressure released. The resultant orange liquid was filtered and washed with ethanol. The filtrate was concentrated in vacuo to give the crude product, which was purified by flash chromatography utilizing heptanes/ethyl acetate (0:100 to 60:40) to give the title compound (72 mg). MS (ES−) 384.1 (M−H)−. 1H NMR (500 MHz, CD3OD) δ 8.07 (s, 1H), 7.78 (s, 1H), 7.36 (d, J=8.78 Hz, 2H), 7.07 (d, J=8.54 Hz, 2H), 4.48 (q, J=7.07 Hz, 2H), 3.80-3.94 (m, 4H), 3.12-3.27 (m, 4H), 1.44 (t, J=7.07 Hz, 3H).

Workup

temperatureThe reaction was cooled
filtrationThe resultant orange liquid was filtered
washwashed with ethanol
concentrationThe filtrate was concentrated in vacuo
customto give the crude product, which
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-a1bf5d19f5e94b368a3a0a59eb6327b9
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

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