Sodium Chloride → 4-[(3-bromo-2-(2-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline

HRID 1198655Notes

Reaction equation

HRID 1198655 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=O)N2)C.[Br:16][C:17]1[C:21]2[CH:22]=[C:23]([CH2:26]Br)[CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[N:35]=[N:36][N:37]([C:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:38]=1.CC(C)([O-:61])C.[K+].O1CCOCCOCCOCCOCCOCC1.[Cl-].[Na+]>O1CCCC1>[Br:16][C:17]1[C:21]2[CH:22]=[C:23]([CH2:26][O:61][C:9]3[C:4]4[CH2:5][CH2:6][CH2:7][CH2:1][C:3]=4[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=3)[CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[N:35]=[N:36][N:37]([C:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:38]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 2855718-Crown-6HCID 189833195-[2-(3-bromo-5-(bromomethyl)benzofuran-2-yl)phenyl]-2-triphenylmethyl-2H-tetrazoleHCID 200942525,7-diethyl-[1,6]naphthyridin-2(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 191027734-[(3-bromo-2-(2-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinolineYield 57.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (291 mg), 5-[2-(3-bromo-5-(bromomethyl)benzofuran-2-yl)phenyl]-2-triphenylmethyl-2H-tetrazole (1.30 g), potassium t-butoxide (168 mg) and 1,4,7,10,13,16-hexaoxacyclooctadecane (40 mg) in dry tetrahydrofuran (15 ml) was stirred under an atmosphere of argon for 18 hours. Saturated sodium chloride solution (25 ml) was added and the mixture was extracted with ether (2×25 ml). The extracts were dried (MgSO4) and concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (3:1 v/v), to give 1-[(3-bromo-2-(2-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methyl]-5,7-diethyl-1,6-naphthyridin-2(1H)-one (A) (640 mg) as a foam; NMR: 1.2(t, 3H), 1.35(t, 3H), 2.7(q, 2H), 3.1(q, 2H), 5.6(s, 2H), 6.8-7.25(m, 19 H), 7.35(s, 1H), 7.5-7.7(m, 3H), 8.0(d, 1H), 8.2(d, 1H).

Workup

  1. extractionthe mixture was extracted with ether (2×25 ml)
  2. dry with materialThe extracts were dried (MgSO4)
  3. concentrationconcentrated by evaporation
  4. customThe residue was purified by flash chromatography
  5. washeluting with ethyl acetate/hexane (3:1 v/v)

Sources & evidence

ORD record
ord-c9b12aead6d64663b9fa99220ba3df81
Source dataset
uspto-grants-1994_01
Patent number
US05281613

Reaction notes

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