Sodium Carbonate → HCID 66797782, compound

HRID 1253946Notes

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[C:28]([OH:31])([CH3:30])[CH3:29].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>[OH:31][C:28]([C:27]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[C:8]1[CH:9]=[CH:10][C:5]2[O:4][C:3](=[O:20])[N:2]([CH3:1])[C:6]=2[CH:7]=1)([CH3:30])[CH3:29]

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 (304 mg, 1.1 mmol), 2-(3-Bromo-pyridin-4-yl)-propan-2-ol (217 mg, 1.0 mmol), Na2CO3 (2 M in water, 1.5 mL, 3.0 mmol) and PdCl2(PPh3)2 (56 mg, 0.08 mmol) in DMF (6 mL) was heated at 100° C. for 4 hrs. After concentration, the residue was diluted with DCM and saturated NH4Cl solution. After filtration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-3.5%) to give the title compound (1.4 mg, 0.5%); ESI-MS m/z: 285 [M+1]+, Retention time 0.98 min; 1H-NMR (CDCl3, 400 MHz) δ 1.51 (s, 6H), 3.43 (s, 3H), 6.95 (d, J=1.6 Hz, 1H), 7.04 (dd, J=8.4, 1.6 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 8.11 (d, J=6.0 Hz, 1H), 8.40 (s, 1H), 8.65 (d. J=6.0 Hz, 1H).

Workup

concentrationAfter concentration
additionthe residue was diluted with DCM and saturated NH4Cl solution
filtrationAfter filtration and concentration
customthe residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-3.5%)

Sources & evidence

ORD record: ord-1d77c678d87e4b5cb6a59ecae591e29e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455522B2

Reaction notes

Loading…