Sodium Acetate → 2-(7-propyl-3,7-dihydro-2H-[1,4]dioxino[2,3-e]indol-9-yl)acetic acid

HRID 1404155Notes

Reaction equation

HRID 1404155 reaction equation
Br[C:2]1[CH:3]=[C:4]2[O:21][CH2:20][CH2:19][O:18][C:5]2=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH3:13])[CH:8]=[C:7]2[CH2:14][C:15]([OH:17])=[O:16].CC([O-])=O.[Na+]>C(OCC)(=O)C.[Pd]>[CH2:11]([N:9]1[C:10]2[C:6](=[C:5]3[O:18][CH2:19][CH2:20][O:21][C:4]3=[CH:3][CH:2]=2)[C:7]([CH2:14][C:15]([OH:17])=[O:16])=[CH:8]1)[CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 669273212-(6-bromo-7-propyl-3,7-dihydro-2H-[1,4]dioxino[2,3-e]indol-9-yl)acetic acid

Product 1

HCID 669271902-(7-propyl-3,7-dihydro-2H-[1,4]dioxino[2,3-e]indol-9-yl)acetic acidYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 40-4 (0.16 g, 0.45 mmol), NaOAc (0.9 g, 0.74 mmol) and 10% Pd/C (0.2 g) in ethyl acetate (20 mL) was stirred under H2 at room temperature for 12 h. The solid was filtered off and the filtrate was concentrated to obtain the desired product 40-5 (0.12 g, 97%) as a yellow solid, which was used in the next step without further purification. LCMS: calc 275.0 found 276.0 [MH]+.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-00ad968556344137b3c8ad93091e9512
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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