Potassium Carbonate → Trifluoroacetic acid

HRID 578638Notes

Reaction equation

HRID 578638 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:14][C:15]([F:25])([F:24])[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20].[C:26]([O-:29])([O-])=[O:27].[K+].[K+]>C(O)(C)C>[F:14][C:15]([F:24])([F:25])[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH:20][C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:26]([OH:29])([C:15]([F:25])([F:24])[F:14])=[O:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 759623-(Trifluoromethyl)benzylamineHCID 66764168HCID 66764168, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 66763182HCID 66763182, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 4-bromoquinoline-8-carbonitrile (100 mg, 0.43 mmol) in 4 mL of isopropanol, 3-(trifluoromethyl)benzylamine (150 mg, 0.85 mmol, 2.0 equiv.) and K2CO3 (119 mg, 0.85 mmol, 2.0 equiv.) were added. The resulting mixture was stirred at 110° C. 2 days. After work-up, the crude was purified by preparative HPLC to yield the title compound as TFA salt in 20% yield. 1HNMR (in MeOD): 4.96 (s, 2H), 6.96 (d, J=7.0 Hz, 1H), 7.58-7.71 (m, 3H), 7.76 (s, 1H), 7.86 (dd, J=7.7 and 8.8 Hz, 1H), 8.39 (d, J=7.3 Hz, 1H), 8.44 (dd, J=1.1 and 7.3 Hz, 1H), 8.75 (dd, J=1.1 and 8.8 Hz, 1H). Mass: M+H+: 328.

Workup

  1. additionwere added
  2. custom2 days
  3. customAfter work-up, the crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-598ef0b6338e4828b4aefb297611502a
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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