HCID 178460905, compound → HCID 178516438, compound

HRID 1784813Notes

Reaction equation

HRID 1784813 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([OH:34])=[N:32][CH:33]=2)[CH:5]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][N:12]3[Si](C(C)C)(C(C)C)C(C)C)[CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([OH:34])=[N:32][CH:33]=2)[CH:5]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][NH:12]3)[CH:7]=1

Participants

3

Reactant 1

HCID 178460905HCID 178460905, compound

Product 1

HCID 178516438HCID 178516438, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 5-[3-hydroxy-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenylamino]-pyridin-2-ol (taken as 0.126 mmol) in TFA/CH2Cl2 (5 mL/5 mL)) was stirred at 0° C. for 1 h. The resulting mixture was concentrated, and saturated aqueous NaHCO3 was added. The pH was adjusted to around 7 and the mixture was extracted with EtOAc (with a small amount of MeOH) several times. After filtering through Celite®, the organic layer was separated, dried and concentrated. Purification by chromatography and further purification by prep-SFC afforded 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridin-2-ol as a brown solid (0.6 mg, 1.5%). 1H NMR (400 MHz, CDCl3): δ 7.62 (dd, J=9.7, 2.8 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 7.28 (d, J=2.9 Hz, 1H), 7.23 (d, J=3.3 Hz, 1H), 7.11 (t, J=7.7 Hz, 1H), 7.01 (d, J=7.2 Hz, 1H), 6.63-6.55 (m, 4H), 6.26 (t, J=2.0 Hz, 1H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additionsaturated aqueous NaHCO3 was added
  3. extractionthe mixture was extracted with EtOAc (with a small amount of MeOH) several times
  4. filtrationAfter filtering through Celite®
  5. customthe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customPurification
  9. customby chromatography and further purification

Sources & evidence

ORD record
ord-f8d0d240a83c41eda633c9e7bf13f4cc
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

Loading…