Trifluoroacetic acid → HCID 15603494, compound

HRID 1784847Notes

Reaction equation

HRID 1784847 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH:17]=[CH:18][N:19]4[Si](C(C)C)(C(C)C)C(C)C)=[CH:11][C:10]=2[C:34]([C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)=[O:35])=CC=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl.CSC>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][NH:19]3)=[CH:11][C:10]=1[C:34]([C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)=[O:35]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68844851HCID 68844851, compound

Product 1

HCID 15603494HCID 15603494, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [2-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone (42 mg, 0.07 mmol) in dichloromethane (0.5 mL) and dimethylsulfide (0.5 mL) at 0° C. was added TFA (1 mL) dropwise. After stirring at 0° C. for 30 mins, the starting material was gone. Saturated aqueous NaHCO3 was added to adjust the pH of the mixture to around 6, and the reaction mixture was extracted with EtOAc several times. The combined EtOAc layers were washed with brine, dried and concentrated. Purification by silica gel column chromatography, followed by further preparative SFC chromatography afforded 3.1 mg (14%) of [2-hydroxy-5-(1H-indol-4-yl)-phenyl]-pyridin-3-yl-methanone as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 11.87 (s, 1H), 9.13-8.89 (m, 1H), 8.88-8.69 (m, 1H), 8.37-8.23 (m, 1H), 8.04 (d, J=7.6 Hz, 1H), 7.91 (dd, J=8.6, 2.1 Hz, 1H), 7.81 (d, J=2.1 Hz, 1H), 7.49-7.40 (m, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.27-7.19 (m, 4H), 7.05 (d, J=7.4 Hz, 1H), 6.57 (s, 1H).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc several times
  2. washThe combined EtOAc layers were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-98563ff731384abeb2265dd327d01442
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

Loading…