Potassium Carbonate → HCID 86719495, compound

HRID 1772260Notes

Reaction equation

HRID 1772260 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18]Cl)[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:20]=1.C(=O)([O-])[O-:22].[K+].[K+].[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)=[CH:32][C:31]=1[C:44]([F:47])([F:46])[F:45])([O-:29])=[O:28]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([C:17](=[O:22])[CH2:18][O:43][C:40]4[CH:39]=[CH:38][C:37]([NH:36][C:33]5[CH:34]=[CH:35][C:30]([N+:27]([O-:29])=[O:28])=[C:31]([C:44]([F:45])([F:46])[F:47])[CH:32]=5)=[CH:42][CH:41]=4)[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86719494HCID 86719494, compoundHCID 86719496HCID 86719496, compound

Product 1

HCID 86719495HCID 86719495, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-[(5-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl]-4-(2-chloroethyl)piperazine (200 mg, 0.61 mmol) in acetonitrile (5 ml) was added potassium carbonate (139 mg, 1.01 mmol, 1.6 eq.), 4-[4-nitro-3-(trifluoromethyl)phenyl]aminophenol (200 mg, 0.67 mmol, 1.1 eq.) and KI (56 mg, 0.34 mmol, 0.6 eq.) with stirring for 3 hours at 70° C. (oil bath). The reaction mixture was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 2% dichloromethane in methanol to afford 1-[4-[(5-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl]piperazin-1-yl]-2-(4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]phenoxy)ethan-1-one as a orange solid (150.3 mg, 36%); (ES, m/z): [M+H]+ 591.15; 1H NMR (300 MHz, CDCl3): δ 7.98 (d, J=9.0 Hz, 1H), 6.91-7.11 (m, 4H), 7.08 (d, J=8.7 Hz, 1H), 7.01 (d, J=8.7 Hz, 2H), 6.92 (dd, J=2.7, 9.0 Hz, 1H), 6.69 (d, J=8.4 Hz, 1H), 6.32 (s, 1H), 4.93-5.09 (m, 1H), 4.75 (s, 2H), 3.65-3.78 (m, 4H), 3.28 (dd, J=9.3, 15.9 Hz, 1H), 2.97 (dd, J=8.1, 15.6 Hz, 1H), 2.79 (dd, J=7.5, 13.5 Hz, 1H), 2.60-2.75 (m, 5H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto give a residue, which
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f48de476fd9d45b1924525f8deba409a
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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