Ethanol → HCID 135457858, compound

HRID 2053444Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:18][C:15]1[CH:14]=[C:13]([C:6]2[C:7](=[O:12])[NH:8][C:9]3[C:4]([C:5]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:3][C:2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:11][CH:10]=3)[O:17][N:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A flask was charged with 6-bromo-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (25 mg, 0.066 mmol)(Example 39), phenyl boronic acid (12 mg, 0.098 mmol), Pd(PPh3)4 (7 mg, 10 mol %), 2 M Na2CO3 (0.25 mL), EtOH (0.25 mL), and toluene (0.5 mL) and heated for 2 hrs at 80° C. The reaction was diluted with EtAc (10 mL) and washed with brine (2×10 mL). The organic layer was concentrated and the title product (12 mg, 50%) eluted from a 5 g SPE with 50% EtAc/hex. 1H NMR (400 MHz, CDCl3) δ 11.42 (s, 1H), 7.82 (dd, 1H), 7.20 (m, 12H), 6.52 (s, 1H), 2.24 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C25H18N2O2 378.1, found 379.1 (M+H).

Workup

additionThe reaction was diluted with EtAc (10 mL)
washwashed with brine (2×10 mL)
concentrationThe organic layer was concentrated
washthe title product (12 mg, 50%) eluted from a 5 g SPE with 50% EtAc/hex

Sources & evidence

ORD record: ord-09ac319e5c8e46c286be1da36e0cdc49
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326788B2

Reaction notes

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