5-Fluoro-8-methylisoquinolin-3-amine → 7-Fluoro-5-(trifluoromethyl)-3-isoquinolinamine

HRID 1672486Notes

Reaction equation

HRID 1672486 reaction equation
FC1C=CC(C)=C2C=1[CH:4]=[C:5]([NH2:13])[N:6]=C2.C(OCC(COCC)C(=N)C(=N)[CH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([F:32])[CH:23]=1)C>>[F:32][C:24]1[CH:23]=[C:22]2[C:27]([CH:4]=[C:5]([NH2:13])[N:6]=[CH:21]2)=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=1

Participants

3

Reactant 2

HCID 592244185-Fluoro-8-methylisoquinolin-3-amineHCID 86639582HCID 86639582, compound

Product 1

HCID 592244247-Fluoro-5-(trifluoromethyl)-3-isoquinolinamineYield 69.4%

Procedure

Scheme O was used for the preparation of 5-fluoro-8-methylisoquinolin-3-amine from 12.0 g of 5-ethoxy-4-(ethoxymethyl)-1-[3-fluoro-5-(trifluoromethyl)phenyl]pentane-2,3-diimine start material to give 5.9 g, yield 69.4%. 1H NMR (400 MHz, DMSO-d6) ppm 6.39 (s, 2H), 6.77 (d, J=1.01 Hz, 1H), 7.91 (dd, J 9.06, 2.52 Hz, 1H), 7.97 (dd, J=8.81, 2.27 Hz, 1H), 8.94 (s, 1H).

Workup

  1. customto give 5.9 g, yield 69.4%

Sources & evidence

ORD record
ord-b5e106ce34a54abb95757aa1ec7d0f2a
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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