Ethanethiol → HCID 53379905, compound

HRID 625965Notes

Reaction equation

HRID 625965 reaction equation
C([O:8][C:9]1[C:10](=[O:29])[N:11]([CH3:28])[CH:12]=[C:13]([C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)[C:14]=1[F:15])C1C=CC=CC=1.C(S)C.B(F)(F)F.CCOCC>C(Cl)Cl.CO>[C:18]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=[C:16]([C:13]2[C:14]([F:15])=[C:9]([OH:8])[C:10](=[O:29])[N:11]([CH3:28])[CH:12]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 67417904HCID 67417904, compound

Product 1

HCID 53379905HCID 53379905, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(benzyloxy)-5-(biphenyl-3-yl)-4-fluoro-1-methylpyridin-2(1H)-one (22 mg, 0.057 mmol) in CH2Cl2 (0.8 mL) was added ethanethiol (53 mg, 0.856 mmol) followed by BF3.OEt2 (0.108 mL, 0.856 mmol). The resulting mixture was stirred at room temperature for 3.5 h, diluted with MeOH and concentrated. Purification by preparative HPLC (10-80% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 13 mg (77%) of 5-biphenyl-3-yl-4-fluoro-3-hydroxy-1-methylpyridin-2(1H)-one as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.61 (d, J=7.9 Hz, 4H), 7.49 (dt, J=22.1, 7.5 Hz, 3H), 7.42-7.35 (m, 2H), 6.99 (d, J=7.9 Hz, 1H), 6.40 (br, 1H), 3.69 (s, 3H). High resolution mass spec (FT/ICR) calc (M+H)+=296.1081 found 296.1081.

Workup

  1. concentrationconcentrated
  2. customPurification
  3. additionby preparative HPLC (10-80% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-dac07436c0d94ad08a7d40ac979306a2
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

Loading…