Toluene → HCID 68491125, compound

HRID 1966211Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH3:62][N:63]1[CH:67]=[CH:66][C:65]([NH2:68])=[N:64]1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:68][C:65]2[CH:66]=[CH:67][N:63]([CH2:62][CH3:16])[N:64]=2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

11.2 5-Benzyloxy-2-bromo-pyridine (0.53 mmol), sodium-tert.-butyl at (1.4 eq.), tris-(dibenzylidene-acetone)-dipalladium (0.01 eq.), BINAP (0.01 eq.) and 1-methyl-1H-pyrazole-3-amine (1.2 eq.) are filled under nitrogen in a microwave reaction vessel. Degassed Toluene (50 eq.) is added. The reaction suspension is heated to 120° C. for 10 min. Ethyl acetate is added to the reaction suspension and filtrated over celite. The solvent of the filtrate is removed in vacuo. “A11” is obtained after column chromatography (heptan/ethyl acetate) as a colourless powder in a yield of 29%; HPLC (method C): 1.60 min); LC-MS (m Method A): 1.008 min, 281.15 (M+H+); 1H-NMR (DMSO-d6, 500 MHz): δ [ppm] 8.859 (s, 1H), 7.886 (d, 1H, J=2.5 Hz), 7.449-7.429 (m, 3H), 7.400-7.370 (m, 2H), 7.342-7.308 (m, 2H), 7.246 (d, 1H, J=9.0 Hz), 6.169 (d, 1H, J=2.5 Hz), 5.062 (s, 2H), 3.709 (s, 3H).

Workup

filtrationfiltrated over celite
customThe solvent of the filtrate is removed in vacuo
custom“A11” is obtained after column chromatography (heptan/ethyl acetate) as a colourless powder in a yield of 29%
custom1.60 min
custom1.008 min, 281.15 (M+H+)

Sources & evidence

ORD record: ord-aae75655c3464f7b9c0b0d10696e8e14
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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