Hydrochloric Acid → HCID 18537514, compound

HRID 412081Notes

Reaction equation

HRID 412081 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[NH:13][CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:16]=1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.Cl.[H][H]>C(O)C.[Pd]>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:15]2[C:16]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[C:12]([CH2:11][CH2:10][CH2:9][OH:8])[NH:13][CH:14]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 18537510HCID 18537510, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18537514HCID 18537514, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(3-benzyloxypropyl)-4-(4-fluorophenyl)-3-(4-pyridyl)pyrrole (0.95 g, 0.0025 mol) in ethanol (125 mL) containing concentrated HCl (0.2 mL) was added to Pd on carbon (0.2 g). This mixture was placed in a hydrogen atmosphere for 16 hours on a Parr hydrogenator at 50 PSI. The mixture was filtered through Celite and triethylamine (0.5 mL) was added to the resulting solution, followed by evaporation in vacuo to give a solid. The solid was extracted into ethyl acetate (100 mL) and washed with water (3×50 mL). The organics were dried over Na2SO4 and evaporated in vacuo to give a light yellow solid (0.7 g, 96% yield). 1HNMR (DMSO-d6) δ 11.10 (1H, s, NH), 8.44 (2H, d), 7.05 (6H, m), 6.91 (1H, d), 4.53 (1H, br s, OH), 3.49 (2H, br s), 2.64 (2H, t), 1.72 (2H, m).

Workup

  1. filtrationThe mixture was filtered through Celite and triethylamine (0.5 mL)
  2. additionwas added to the resulting solution
  3. customfollowed by evaporation in vacuo
  4. customto give a solid
  5. extractionThe solid was extracted into ethyl acetate (100 mL)
  6. washwashed with water (3×50 mL)
  7. dry with materialThe organics were dried over Na2SO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-2047719a017941f893d63be7a934a41b
Source dataset
uspto-grants-2003_05
Patent number
US06562843B1

Reaction notes

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