Sodium Cyanide → HCID 136018659, compound

HRID 2053445Notes

Reaction equation

HRID 2053445 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]#[N:26].[Na+]>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.CC#N>[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]#[N:26])=[CH:11][CH:10]=3)[O:17][N:16]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 135537661HCID 135537661, compound

Product 1

HCID 136018659HCID 136018659, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 6-bromo-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (30 mg, 0.077 mmol)(example 39), Pd(PPh3)4 (5 mg, 5 mol %), NaCN (8 mg, 0.16 mmol), Cul (1.5 mg, 10 mol %), and 0.7 mL CH3CN and heated in a sealed tube in a microwave reactor at 100° C. for 1 hr. The title compound was obtained by elution from a 10 g SPE with 50% EtAc/hex to give 13 mg (50%) of a white solid. 1H NMR (400 MHz, CD3OD) δ 7.78 (dd, 1H), 7.50 (m, 5H), 7.28 (m, 2H), 6.42 (s, 1H), 2.20 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C20H13N3O2 327.1, found 328.1 (M+H).

Sources & evidence

ORD record
ord-b5592bff69a04fe3b590fd6c0a0b3683
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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