Morpholine → HCID 66747691, compound

HRID 2402142Notes

Reaction equation

HRID 2402142 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH3:11])[C:3]=1[C:12]#[N:13].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1>[C:12]([C:3]1[C:4]([CH3:11])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[S:6][C:2]=1[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)#[N:13]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 66747919HCID 66747919, compound

Product 1

HCID 66747691HCID 66747691, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 5-bromo-4-cyano-3-methylthiophene-2-carboxylate (6.29 g, 24.2 mmol), morpholine (2.53 g, 29.0 mmol) and cesium carbonate (15.8 g, 48.4 mmol) in anhydrous Tetrahydrofuran (110 mL) was heated to reflux for 19 hours, and then cooled to room temperature. The mixture was filtered and washed with DCM. The filtrate was rotavaped with Celite. The coated Celite was dry loaded in a silica gel cartridge and chromatographed using MeOH/DCM (1/99) to give a white solid product (4.70 g, yield 73%). LC/MS: (FA) ES+ 267. 1H NMR (400 MHz, d-chloroform) δ 3.85 (m, 4H), 3.82 (s, 3H), 3.58 (m, 4H), 2.56 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 19 hours
  3. filtrationThe mixture was filtered
  4. washwashed with DCM
  5. customThe coated Celite was dry
  6. customchromatographed

Sources & evidence

ORD record
ord-7ab64d126dd1419ea784e10f4cfd533b
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

Loading…