Pyridine → HCID 131726137, compound

HRID 856924Notes

Reaction equation

HRID 856924 reaction equation
F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:4][CH:3]=1.FC1C2C(=CC=CC=2)C(S([Cl:39])(=O)=O)=CC=1.[NH:40]1[C:49]2[C:44](=CC=CC=2)C[CH2:42][CH2:41]1.[N:50]1C=CC=CC=1>C(Cl)Cl>[ClH:39].[N:15]1([S:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([N:40]3[CH2:41][CH2:42][NH:50][CH2:44][CH2:49]3)=[CH:3][CH:4]=2)(=[O:14])=[O:13])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 694601,2,3,4-TetrahydroquinolineHCID 27746474-fluoronaphthalene-1-sulfonyl ChlorideHCID 21864873HCID 21864873, compound

Product 1

HCID 131726137HCID 131726137, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-[(4-Fluoro-1-naphthyl)sulfonyl]-1,2,3,4-tetrahydroquinoline—Method E: To a stirred solution of 4-fluoronaphthalene-1-sulfonyl chloride (200 mg, 0.82 mmol) in DCM (1 ml) was added 1,2,3,4-tetrahydroquinoline (123 μl, 0.98 mmol) followed by pyridine (0.25 ml). The reaction mixture was stirred over night, diluted with DCM and washed with 1M HCl (3×3 ml). Subsequent drying of the organic phase using MgSO4, and removal of the solvents in vacuo afforded the title compound (280 mg, 100%) as a white solid. 1H NMR (CDCl3) δ 8.24–8.10 (m, 3H), 7.68–7.62 (m, 1H), 7.58–7.51 (m, 1H), 7.42–7.34 (m, 1H), 7.23–7.04 (m, 3H), 6.96–6.89 (m, 1H), 3.84–3.74 (m, 2H), 2.39–2.28 (m, 2H), 1.63–1.49 (m, 1H); MS m/z (M+1) 342.

Workup

  1. washwashed with 1M HCl (3×3 ml)
  2. customSubsequent drying of the organic phase
  3. customMgSO4, and removal of the solvents in vacuo

Sources & evidence

ORD record
ord-109a76d452f64551917d229f2ff59fe6
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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