HCID 86299111, compound → HCID 86299112, compound

HRID 589038Notes

Reaction equation

HRID 589038 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:21]2[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=2)[C:5]2[O:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:7]3[C:17](=[O:20])[NH:18][C:19]=1[C:6]=23.[Cl-].[CH3:28][Zn+]>C1COCC1.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>[CH3:28][C:2]1[CH:3]=[C:4]([C:21]2[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=2)[C:5]2[O:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:7]3[C:17](=[O:20])[NH:18][C:19]=1[C:6]=23

Participants

5

Reactant 2

HCID 86299111HCID 86299111, compoundHCID 178477797HCID 178477797, compound

Product 1

HCID 86299112HCID 86299112, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A reaction mixture of 9-bromo-7-(1-methyl-1H-pyrazol-5-yl)-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (17 mg, 0.04 mmol), a solution of 2.0 M methylzinc chloride in THF (0.10 mL) and tetrakis(triphenylphosphine)palladium(0) (2 mg, 0.002 mmol) in THF (0.5 mL) under nitrogen was heated in a microwave at 130° C. for 5 min. The title compound was purified by preparative LCMS using a pH10 buffer. LCMS calc. for C20H19N4O2 (M+H)+: m/z=347.1. found: 347.2.

Workup

  1. customThe title compound was purified by preparative LCMS

Sources & evidence

ORD record
ord-2efba51d5f7b4b82860600062a206f67
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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