Ethanol → HCID 86698824, compound

HRID 338490Notes

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-2f0df178b6304e44a95b3e13ca83e675
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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