Sodium Carbonate → 3-methyl-5-(4-(oxetan-2-yl)pyridin-3-yl)benzo[d]oxazol-2(3H)-one

HRID 1253945Notes

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:20].Br[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[CH:28]1[CH2:31][CH2:30][O:29]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][C:27]=3[CH:28]3[CH2:31][CH2:30][O:29]3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-benzooxazol-2-one (123 mg, 0.44 mmol), 3-Bromo-4-oxetan-2-yl-pyridine (96 mg, 0.44 mmol), Na2CO3 (2 M in water, 067 mL, 1.35 mmol) and PdCl2(PPh3)2 (16 mg, 0.02 mmol) in DMF (4 mL) was heated at 100° C. for 3 h. After concentration, the resulting residue was diluted with DCM and saturated NH4Cl solution. After filteration, the filtrates were concentrated and the residue was purified by flash column (MeOH/CH2Cl2, v/v, 0-3.5%) and afforded the title compound (6 mg, 5%); ESI-MS m/z: 283 [M+1]+, Retention time 1.03 min; 1HNMR (MeOD, 400.342 MHz) δ ppm 2.60-2.65 (m, 1H), 2.83-2.87 (m, 1H), 3.47 (s, 3H), 4.62-4.68 (m, 1H), 4.75-4.82 (m, 1H), 5.91 (t, J=7.6 Hz, 1H), 7.06 (dd, J=8, 1.6 Hz, 1H), 7.15 (d, J=1.6 Hz, 1H), 7.39 (d, J=8 Hz, 1H), 7.94 (d, J=5.2 Hz, 1H), 8.46 (s, 1H), 8.67 (d, J=5.2 Hz, 1H).

Workup

concentrationAfter concentration
additionthe resulting residue was diluted with DCM and saturated NH4Cl solution
concentrationAfter filteration, the filtrates were concentrated
customthe residue was purified by flash column (MeOH/CH2Cl2, v/v, 0-3.5%)

Sources & evidence

ORD record: ord-99e5c183b34148ceb62077a4e2fef0f5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455522B2

Reaction notes

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