Water → HCID 67094419, compound

HRID 1881236Notes

Reaction equation

HRID 1881236 reaction equation
[Br:1][C:2]1[C:7]2[S:8][C:9]([C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])=[C:10]([Cl:11])[C:6]=2[CH:5]=[C:4]([O:20][CH3:21])[C:3]=1[OH:22].[CH:23](N(C(C)C)CC)(C)C.O>CN1CCCC1=O>[Br:1][C:2]1[C:7]2[S:8][C:9]([C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[O:13])=[C:10]([Cl:11])[C:6]=2[CH:5]=[C:4]([O:20][CH3:21])[C:3]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 81531DiisopropylethylamineHCID 67094310HCID 67094310, compound

Product 1

HCID 67094419HCID 67094419, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

(7-Bromo-3-chloro-6-hydroxy-5-methoxy-benzo[b]thiophen-2-yl)-morpholin-4-yl-methanone (7.0 g) was dissolved in 1-methyl-2-pyrrolidinone (35 ml) and di-isopropylethylamine was gradually added. The reaction solution was warmed at 80° C. for 3 hours. Then water (350 ml) was added. The reaction solution was stirred at room temperature for 30 minutes. The product was extracted into ethyl acetate. The organic phase was washed with 1M hydrochloric acid and a solution of sodium sulphate, evaporated and dried in vacuum. The product was purified by flash chromatography using heptane-ethyl acetate as an eluent.

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washThe organic phase was washed with 1M hydrochloric acid
  3. customa solution of sodium sulphate, evaporated
  4. customdried in vacuum
  5. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-b3918050670c413384c0d8a2353b0235
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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