Boron tribromide → 5-(4-Chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505814Notes

Reaction equation

HRID 505814 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[C:11]3[CH:22]=[C:23]([C:25]([O:27]C)=[O:26])[S:24][C:10]=3[C:9]=2[CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[C:11]3[CH:22]=[C:23]([C:25]([OH:27])=[O:26])[S:24][C:10]=3[C:9]=2[CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromide2×HCID 11432036methyl 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 113177625-(4-Chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acidYield 47%

Procedure

A solution (0.1 M) of methyl 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate was treated with BBr3 (4 eq.) and the mixture was stirred at RT. After 1 h an additional quantity of BBr3 (2 eq.) was added and the mixture was stirred at RT for 1 h, then quenched with aqueous HCl (1 N) and extracted with AcOEt. The combined organic phase was dried and solvent was evaporated under reduced pressure to give a residue which was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 10 micron, 19×150 mm; flow: 20 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 90% A isocratic for 2 min then linear to 10% A in 9 min) to afford the title compound (47%) as a solid.

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. customquenched with aqueous HCl (1 N)
  3. extractionextracted with AcOEt
  4. customThe combined organic phase was dried
  5. customsolvent was evaporated under reduced pressure
  6. customto give a residue which
  7. customwas purified by RP-HPLC (Conditions

Sources & evidence

ORD record
ord-7dd3ff67856f4aebb4c56295f06d4eb8
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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