2-Chloroethanol → HCID 58102871, compound

HRID 384983Notes

Reaction equation

HRID 384983 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12](=[O:27])[N:13]([CH:17]3[C:25]4[C:20](=[C:21]([OH:26])[CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:35][CH2:36][OH:37]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12](=[O:27])[N:13]([CH:17]3[C:25]4[C:20](=[C:21]([O:26][CH2:35][CH2:36][OH:37])[CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 58102874HCID 58102874, compound

Product 1

HCID 58102871HCID 58102871, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-bromophenyl)-1-(4-hydroxy-2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide (30 mg, 0.071 mmol) in DMF (0.2 mL) was added K2CO3 (30 mg, 0.22 mmol) and 2-chloroethanol (9.3 uL, 0.14 mmol). The reaction mixture was heated at 70 C overnight. It was filtered and purified by prep HPLC to afford N-(4-bromophenyl)-1-(4-(2-hydroxyethoxy)-2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide (20 mg, 60%). Retention time (min)=7.588, method [7], MS (ESI) 469.1 (M+H); 1H NMR (300 MHz, CDCl3) δ 12.20 (s, 1H), 8.57 (dd, J=2.1 Hz, 6.9 Hz, 1H), 7.65 (d, J=9.0 Hz, 2H), 7.44 (d, J=9.0 Hz, 2H), 7.15-7.30 (overlap with CDCl3, 2H), 6.83 (d, J=8.1 Hz, 1H), 6.73 (d, J=7.5 Hz, 1H), 6.58 (dd, J=5.4 Hz, 8.4 Hz, 1H), 6.39 (t, J=6.9 Hz, 1H), 4.14 (m, 2H), 4.00 (m, 2H), 2.78-3.15 (m, 3H), 1.90-2.10 (m, 1H).

Workup

  1. temperatureThe reaction mixture was heated at 70 C overnight
  2. filtrationIt was filtered
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-e02aa813f37b4cf5845c54bdef74044b
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Reaction notes

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