Butylamine → HCID 58998497, compound

HRID 1593073Notes

Reaction equation

HRID 1593073 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15](=[O:20])[N:14]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23](Br)[CH:22]=1)[CH:13]=[CH:12]2)[CH3:8])([CH3:4])([CH3:3])[CH3:2].Br[C:33]1[CH:38]=[C:37](F)C=C[C:34]=1[N+:40]([O-])=O.[Si](C#C)(C)(C)C.C(N)CCC>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.[Cu]I.CN(C=O)C>[C:1]([O:5][C:6](=[O:31])[N:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15](=[O:20])[N:14]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([NH:40][CH2:34][CH2:33][CH2:38][CH3:37])[CH:22]=1)[CH:13]=[CH:12]2)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8007ButylamineHCID 66111TrimethylsilylacetyleneHCID 27569932-Bromo-4-fluoro-1-nitrobenzeneHCID 58998403HCID 58998403, compound2×

Product 1

HCID 58998497HCID 58998497, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

[2-(3-Bromo-4-nitro-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester was generated by Method A (Example 46) using 2-bromo-4-fluoro-1-nitro-benzene. A mixture of [2-(3-Bromo-4-nitro-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester (21 mg, 0.0427 mmol), tetrakis(triphenylphosphine)palladium(0) (2.5 mg, 0.002 mmol), copper (I) iodide (2 mg, 0.008 mmol), TMS acetylene (10 ul, 0.07 mmol), n-butylamine (1.5 ml) and 1 mL DMF was purged with argon for 2 minutes. The mixture was then subjected to microwave irradiation (120° C.) for 5 minutes, then diluted with ethyl acetate and washed with brine. The organic layers were combined and concentrated in vacuo to give a crude residue, which was purified by column chromatography (silica 5-25% EtOAc/hexane) to give [2-(3-butylamino-4-nitro-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester.

Workup

  1. customwas purged with argon for 2 minutes
  2. customThe mixture was then subjected to microwave irradiation (120° C.) for 5 minutes
  3. additiondiluted with ethyl acetate
  4. washwashed with brine
  5. concentrationconcentrated in vacuo
  6. customto give a crude residue, which
  7. customwas purified by column chromatography (silica 5-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-c61802730bd24f2298b7f6441f6b3b8e
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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