Methyl Thioglycolate → HCID 69916910, compound

HRID 1836436Notes

Reaction equation

HRID 1836436 reaction equation
Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[CH3:18]C(C)([O-])C.[K+].[C:24]([O:28][CH3:29])(=[O:27])[CH2:25][SH:26]>C1COCC1>[CH2:29]([O:28][C:24](=[O:27])[CH2:25][S:26][C:2]1[CH:17]=[CH:16][C:5]([C:6](=[O:7])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][N:3]=1)[CH3:18]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 2653166HCID 2653166, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69916910HCID 69916910, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-N-(4-fluoro-phenyl)-nicotinamide (0.21 g, 0.84 mmol) in 5 mL of THF was added potassium tert-butoxide (0.19 g, 1.68 mmol) in one portion and stirred for 1 minute. To the suspension was added methyl thioglycolate (0.15 mL, 1.68 mmol) dropwise over 1 minute. The mixture was stirred for 12 h then poured into ice water and the solids collected. Purification by trituration using ethyl acetate/hexanes gave 88 mg (33%) of the desired product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.36 (s 1H), 8.90 (m, 1H), 8.11 (m, 1H), 7.74 (m, 2H), 7.48 (m, 1H), 7.17 (m, 2H), 4.10 (s, 2H), 3.63 (s, 3H); MS (EI) m/z 319.13 (M−H)−.

Workup

  1. stirringThe mixture was stirred for 12 h
  2. customthe solids collected
  3. customPurification by trituration

Sources & evidence

ORD record
ord-ca11320c4adb4d9ab8d7a99b0c1d37ae
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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