Pyrrole → ethyl 6-chloro-7-(ethoxymethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854979Notes

Reaction equation

HRID 854979 reaction equation
N1C=CC=C1.[H-].[Na+].Br[CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:16]([C:20]([F:23])([F:22])[F:21])[O:17]2)=[CH:12][C:11]=1[Cl:29].C[O:31][CH2:32][CH2:33]OC>>[Cl:29][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:10]=1[CH2:9][O:31][CH2:32][CH3:33])[O:17][CH:16]([C:20]([F:23])([F:22])[F:21])[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:14]2

Participants

5

Reactant 4

HCID 8027PyrroleHCID 80711,2-Dimethoxyethane3×HCID 24758Sodium hydrideHCID 69517129ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69518622ethyl 6-chloro-7-(ethoxymethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Conditions

Temperature
0 °C

Procedure

A solution of pyrrole (55 mg, 0.75 mmol) in 1.5 mL DME was added to a mixture of NaH (38 mg, 0.83 mmol) in I mL DME at 0° C. under argon. The mixture was stirred at 0° C. for 10 min and then warmed to 25° C. After 30 min, a solution of ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate (300 mg, 0.75 mmol), from Example 162 Step 3, was dissolved in 2.5 mL DME was added dropwise. After 3 h, the reaction was filtered through a pad of Celite (1″) and washed with EtOAc (10 mL). The filtrate was concentrated to give a brown oil in 350 mg (100%).

Workup

  1. customat 0° C.
  2. temperaturewarmed to 25° C
  3. waitAfter 30 min
  4. additionwas added dropwise
  5. waitAfter 3 h
  6. filtrationthe reaction was filtered through a pad of Celite (1″) and
  7. washwashed with EtOAc (10 mL)
  8. concentrationThe filtrate was concentrated
  9. customto give a brown oil in 350 mg (100%)

Sources & evidence

ORD record
ord-816c202128ce417e81383f0ca0a5d982
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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