Hydrochloric Acid → 2-(5-fluoro-4-hydroxy-1-methyl-1H-indol-3-yl)-N-methylacetamide

HRID 1404138Notes

Reaction equation

HRID 1404138 reaction equation
C([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15](Br)=[C:14]2[C:10]=1[C:11]([CH2:21][C:22]([NH:24][CH3:25])=[O:23])=[CH:12][N:13]2[CH3:20])C1C=CC=CC=1.N1C=CC=CC=1.Cl>CO.[Pd]>[F:18][C:17]1[C:9]([OH:8])=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:20])[CH:12]=[C:11]2[CH2:21][C:22]([NH:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 583040222-(4-(benzyloxy)-7-bromo-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl acetamide

Product 1

HCID 583040072-(5-fluoro-4-hydroxy-1-methyl-1H-indol-3-yl)-N-methylacetamideYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 33-5 (1.4 g, 4.5 mmol), pyridine (2 mL) and Pd/C (140 mg, 10%) in methanol (20 mL) was stirred at room temperature overnight under hydrogen atmosphere. The mixture was adjusted with hydrochloric acid to pH=5-6. The solid was filtered off and the filtrate was concentrated. The resulting residue was partitioned between water (20 mL) and ethylacetate (20 mL). The organic layer was separated, washed with brine (3×30 mL), dried over MgSO4, filtered and evaporated to obtain 33-6 (700 mg, 85%) as a brown solid. LRMS: calc 236.1 and found: 237.1 [M+1].

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was partitioned between water (20 mL) and ethylacetate (20 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (3×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-359afddcd28b4008b201347ecfc3b8d5
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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