Sodium Hydroxide → HCID 59864771, compound

HRID 2423282Notes

Reaction equation

HRID 2423282 reaction equation
NC1C(OC2C=CC(CC(O)=O)=CC=2Cl)=CC=C2C=1C=C(CCC)N2.NC1C(OC2C=CC(CC(O)=O)=CC=2Cl)=CC=C2C=1C(CC)=C(C)N2.NC1C=C2C(C(CC)=C(C)N2)=CC=1OC1C=CC(CC(O)=O)=CC=1Cl.[Cl:76][C:77]1[CH:78]=[C:79]([CH2:99][C:100]([OH:102])=[O:101])[CH:80]=[CH:81][C:82]=1[O:83][C:84]1[CH:85]=[C:86]2[C:90](=[CH:91][C:92]=1[N+:93]([O-:95])=[O:94])[NH:89]C(C)=C2CC.O.O.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[NH2:89][C:90]1[CH:86]=[CH:85][C:84]([O:83][C:82]2[CH:81]=[CH:80][C:79]([CH2:99][C:100]([OH:102])=[O:101])=[CH:78][C:77]=2[Cl:76])=[C:92]([N+:93]([O-:95])=[O:94])[CH:91]=1

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 59864783HCID 59864783, compoundHCID 59864789HCID 59864789, compoundHCID 59864820HCID 59864820, compoundHCID 59864907HCID 59864907, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59864771HCID 59864771, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

2-(4-(4-Amino-2-propyl-1H-indol-5-yloxy)-3-chlorophenyl)acetic acid, 2-(4-(4-amino-3-ethyl-2-methyl-1H-indol-5-yloxy)-3-chlorophenyl)acetic acid and 2-(4-(6-amino-3-ethyl-2-methyl-1H-indol-5-yloxy)-3-chlorophenyl)acetic acid (7.3). A solution of the mixture of regioisomers 7.2 (1.30 g, 3.34 mmol) and tin chloride dihydrate 3.02 g, 13.4 mmol) dissolved in ethyl acetate (10 mL) was heated to 90° C. (external temperature, oil bath) in a capped vial overnight. The reaction solution was poured into aqueous 1N sodium hydroxide solution and the resulting bi-phase passed through a pad of Celite, rinsing with water and ethyl acetate. The filtrate was acidified to pH<4 with 1N hydrochloric acid solution and the organic layer separated and washed with water and brine then stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator. The regioisomers were isolated by semi-preparative reversed phase HPLC to afford regioisomer A as a brown solid and regioisomer B as a brown solid and regioisomer C as a brown solid. LC-MS ESI (pos.) m/z: 359.0 (M+H).

Workup

  1. washrinsing with water and ethyl acetate
  2. customthe organic layer separated
  3. washwashed with water and brine
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  6. customThe regioisomers were isolated by semi-preparative reversed phase HPLC
  7. customto afford regioisomer A as a brown solid and regioisomer B as a brown solid and regioisomer C as a brown solid

Sources & evidence

ORD record
ord-42c95f04e4474b5c8a2d574c7e2097ae
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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