Benzyl Alcohol → HCID 58286938, compound

HRID 1962396Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[C:5](=[O:13])[N:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:3]=1[CH3:20].[CH2:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C3[O:48][C:47]4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:21]([O:28][C:47]([C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[C:5](=[O:13])[N:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:3]=1[CH3:20])=[O:48])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Bromo-8-fluoro-3-methyl-2-pyridin-3-yl-2H-isoquinolin-1-one (320 mg, 0.96 mmol) and benzyl alcohol (300 μL, 2.90 mmol) were added to palladium (II) acetate (22 mg, 0.096 mmol) and 4,5-bis-diphenylphosphanyl-9,9-dimethyl-9H-xanthene (56 mg, 0.096 mmol) and sodium carbonate (305 mg, 2.88 mmol) in toluene (3 mL). The reaction mixture was stirred under an atmosphere of carbon monoxide at 100° C. for 2 days. The reaction mixture was poured onto a 25 g silica gel column and it was flash chromatographed (gradient: heptane-ethyl acetate) to give the title compound (151 mg, yield 40.5%). LC-MS (m/z) 389.2 (MH+); tR=1.15. 1H NMR (500 MHz, CDCl3): 1.96 (s, 3H, Me), 5.42 (s, 2H), 7.12 (dd, J=8.3 Hz, J=10.9 Hz, 1H), 7.31 (d, J=8.2 Hz, 1H), 7.35-7.42 (m, 3H), 7.43-7.5 (m, 3H), 7.55-7.63 (m, 2H), 8.5 (d, J=2.1 Hz, 1H), 8.71 (dd, J=4.7 Hz, J=1 Hz, 1H).

Workup

additionThe reaction mixture was poured onto a 25 g silica gel column and it
customchromatographed (gradient: heptane-ethyl acetate)

Sources & evidence

ORD record: ord-1e6451612b06451d9bf87c0b9879d088
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415356B2

Reaction notes

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