Cesium carbonate → 2-(6'-methoxy-7',8'-dimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinoline]-1'-yl)benzo[d]thiazole

HRID 2103092Notes

Reaction equation

HRID 2103092 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH3:22])[C:19]=2[CH3:21])[CH2:14][C:13]2([CH2:27][CH2:26][CH2:25]2)[CH2:12]1)=[S:10].C([O-])([O-])=O.[Cs+].[Cs+]>[Cu](I)I.O(CCOC)C>[CH3:24][O:23][C:17]1[CH:16]=[C:15]2[C:20](=[C:19]([CH3:21])[C:18]=1[CH3:22])[N:11]([C:9]1[S:10][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N:8]=1)[CH2:12][C:13]1([CH2:27][CH2:26][CH2:25]1)[CH2:14]2

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86605501HCID 86605501, compound

Product 1

HCID 690570362-(6'-methoxy-7',8'-dimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinoline]-1'-yl)benzo[d]thiazoleYield 91.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture was made of N-(2-bromophenyl)-6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-carbothioamide (200 mg), Cs2CO3 (176 mg), copper iodide (8.5 mg) 1,10-phenanthioline (16.2 mg) and 2 mL 1,2 dimethoxylethane. The mixture was then heated up in a 90° C. oil bath for 1 hour, filtered and evaporated. The residue was passed through a silica gel column (hexane:dichloromethane=10:1), 2-(6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)benzo[d]thiazole (150 mg) was obtained. 1H-NMR (300 MHz, CDCl3) δ=7.86-6.58 (d, J=8.1 Hz, 1H); 6.58-6.44 (m, 1H); 7.41-7.19 (m, 1H); 7.17-6.96 (m, 1H); 6.64 (s, 1H); 3.87 (s, 3H); 2.76 (s, 2H); 2.18 (s, 3H); 2.17 (s, 3H); 1.96-1.52 (m, 6H) ppm.

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-22e5aec821394a15a171979d5f0674c0
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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