Sodium Carbonate → HCID 86663361, compound

HRID 1253948Notes

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]=[C:26]([F:30])[C:27]=1[CH:28]=[O: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>[F:30][C:26]1[CH:25]=[N:24][CH:23]=[C:22]([C:8]2[CH:9]=[CH:10][C:5]3[O:4][C:3](=[O:20])[N:2]([CH3:1])[C:6]=3[CH:7]=2)[C:27]=1[CH:28]=[O: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 (138 mg, 0.5 mmol), 3-Bromo-5-fluoro-pyridine-4-carbaldehyde (102 mg, 0.5 mmol), Na2CO3 (2 M in water, 0.75 mL, 1.5 mmol) and PdCl2(PPh3)2 (17 mg, 0.03 mmol) in DMF (3 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, 0-1.5%) and afforded the title compound (47 mg, 35%). 1H NMR (400.3 MHz, CDCl3): δ 3.45 (s, 3H), 6.96 (d, J=1.7 Hz, 1H), 7.08 (dd, J=8, 1.7 Hz, 1H), 7.32 (d, J=8 Hz, 1H) 8.59 (s, 1H), 8.68 (d, J=1.3 Hz, 1H), 10.07 (s, 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, 0-1.5%)

Sources & evidence

ORD record: ord-3a01f5c5f44e4df09531d5fbcecea7b5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455522B2

Reaction notes

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