Potassium Carbonate → HCID 10188544, compound

HRID 968371Notes

Reaction equation

HRID 968371 reaction equation
[CH3:1][CH:2]([CH3:28])[CH2:3][C@H:4]([C:20]1([C:25]([NH2:27])=[O:26])[CH2:24][CH:23]=[CH:22][CH2:21]1)[C:5](=[O:19])[NH:6][CH:7]1[C:13](=[O:14])[NH:12][C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[CH2:9][CH2:8]1.C([O-])([O-])=O.[K+].[K+].[F:35][C:36]1[CH:50]=[CH:49][CH:48]=[CH:47][C:37]=1[O:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42]Br>CC#N>[F:35][C:36]1[CH:50]=[CH:49][CH:48]=[CH:47][C:37]=1[O:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42][N:12]1[C:13](=[O:14])[CH:7]([NH:6][C:5]([CH:4]([C:20]2([C:25]([NH2:27])=[O:26])[CH2:21][CH:22]=[CH:23][CH2:24]2)[CH2:3][CH:2]([CH3:28])[CH3:1])=[O:19])[CH2:8][CH2:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27374543-(2-Fluorophenoxy)benzyl BromideHCID 59033282HCID 59033282, compound

Product 1

HCID 10188544HCID 10188544, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 20 (11 mg) in CH3CN (2 mL) was added K2CO3 (8 mg) and 3-(2-fluorophenoxy)benzyl bromide 22 (12 mg). The reaction mixture was stirred at rt for 20 hrs before the solvent was removed under pressure. The crude product was purified by flash chromatography to give compound 23 (77%, 13 mg). 1H NMR (300 MHz, CDCl3) 7.32-6.80 (m, 12H), 5.72 (m, 1H), 5.58 (m, 1H), 5.34 (d, 1H), 4.72 (d, 1H), 4.48 (m, 1H), 3.18 (m, 1H), 2.70-2.20 (m, 8H), 1.95-1.78 (m, 2H), 1.42 (m, 1H), 1.12 (m, 1H), 0.92-0.80 (q, 6H); MS [M+H]+ 584.

Workup

  1. customwas removed under pressure
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-872e08c283a441ddbfd789bafb5b2d14
Source dataset
uspto-grants-2005_10
Patent number
US06958329B2

Reaction notes

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