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Sodium hydride → HCID 18952386, compound

HRID 1492309
Notes
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Reaction equation

HRID 1492309 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[N:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:28])[N:10]2[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][CH2:26][CH3:27])[CH:19]=1)[CH3:4].[CH3:29][O:30][C:31](=[O:40])[CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)Br>O1CCCC1>[CH2:3]([C:5]1[N:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:28])[N:10]2[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[CH2:32][C:31]([O:30][CH3:29])=[O:40])=[C:20]([CH2:25][CH2:26][CH3:27])[CH:19]=1)[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 189523935,7-diethyl-1-(4-hydroxy-3-propylbenzyl)-1,6-naphthyridin-2(1H)-one

Product 1

HCID 18952386HCID 18952386, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
2×

Procedure

Sodium hydride (60% dispersion in oil, 51 mg) was added to a solution of compound F (440 mg) in tetrahydrofuran (15 ml) under an atmosphere of argon. The mixture was stirred for 20 minutes and then methyl-α-bromophenylacetate (320 mg) in tetrahydrofuran (5 ml) was added. The mixture was stirred for 18 hours and then volatile material was removed by evaporation. The residue was partitioned between ethyl acetate (25 ml) and water (25 ml) and the organic layer was separated, washed with saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/dichloromethane (1:199 v/v) to give methyl 2-[4-((5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl)-2-propylphenoxy]phenylacetate (A) (300 mg) as an oil; NMR: 0.9(t, 3H), 1.2(t, 3H), 1.35(t, 3H), 1.55-1.7(m, 2H), 2.7(t, 2H), 2.8(q, 2H), 3.1(q, 2H), 5.4(s, 2H), 5.6(s, 1H), 6.65(d, 1H), 6.75(d, 1H), 6.9(s, 1H), 6.95(d, 1H), 7.1(s, 1H), 7.3-7.4(m, 3H), 7.5-7.6(m, 2H), 7.95(d, 1H).

Workup

  1. stirringThe mixture was stirred for 18 hours
  2. customvolatile material was removed by evaporation
  3. customThe residue was partitioned between ethyl acetate (25 ml) and water (25 ml)
  4. customthe organic layer was separated
  5. washwashed with saturated sodium chloride solution (25 ml)
  6. dry with materialdried (MgSO4)
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified by flash chromatography
  9. washeluting with methanol/dichloromethane (1:199 v/v)

Sources & evidence

ORD record
ord-0425e7e9855b44bc927b773ef51cf2e2
Source dataset
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05373015

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes