Cesium carbonate → HCID 59577780, compound

HRID 1947447Notes

Reaction equation

HRID 1947447 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:18]1[S:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1>CC#N>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][C:18]3[S:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH:10]=2)[CH:6]=[CH:7]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 119872-ChlorobenzothiazoleHCID 5245086-Hydroxyindole

Product 1

HCID 59577780HCID 59577780, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 6-hydroxyindole (5.0 g, 37.6 mmol) and Cs2CO3 (36.7 g, 112.8 mmol) in MeCN (75 mL) was added 2-chlorobenzthiazole (6.4 g, 4.7 mL, 37.6 mmol) and the resulting suspension was stirred (rt, 2 d). The reaction mixture was partitioned with brine and EtOAc (200 mL each) and the aqueous layer was extracted with EtOAc (200 mL). The organic layers were combined, washed with brine (300 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using EtOAc:hexane (0-40%) to afford the title compound as a tan solid (6.1 g, 61%). MS (ESI): mass calcd. for C15H10N2OS, 266.3; m/z found, 267.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (s, 1H), 7.72 (dd, J=8.4, 0.6, 1H), 7.65-7.63 (m, 2H), 7.39-7.35 (m, 2H), 7.27-7.22 (m, 1H), 7.19-7.18 (m, 1H), 7.08 (dd, J=8.4, 2.1, 1H), 6.55-6.53 (m, 1H).

Workup

  1. customThe reaction mixture was partitioned with brine and EtOAc (200 mL each)
  2. extractionthe aqueous layer was extracted with EtOAc (200 mL)
  3. washwashed with brine (300 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68831b19b2834968b12ad0619cd85190
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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