Water → HCID 68903330, compound

HRID 735354Notes

Reaction equation

HRID 735354 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:21]2[C:26](/[CH:27]=[N:28]/[S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])=[CH:25][CH:24]=[CH:23][N:22]=2)(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:21]2[C:26]([CH2:27][NH:28][S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])=[CH:25][CH:24]=[CH:23][N:22]=2)(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 87616494HCID 87616494, compound

Product 1

HCID 68903330HCID 68903330, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1E)-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}pyridin-3-yl)methylene]-2-methylpropane-2-sulfinamide (170 mg, 0.34 mmol) in MeOH (1.2 ml) and CH2Cl2 (2.5 ml) was added NaBH4 (78 mg, 2.06 mmol). The reaction was left for 10 minutes, before addition of water (2 mL). The mixture was extracted with CH2Cl2 dried (Na2SO4) and evaporated in vacuo to give the title compound as a solid (125 mg). 1H NMR (400 MHz, d6-DMSO): δ 8.72 (1H, s), 8.43 (1H, t, J=2.3 Hz), 8.38 (1H, s), 8.34 (1H, d, J=8.7 Hz), 8.23 (2H, dd, J=8.2, 10.2 Hz), 8.04 (1H, dd, J=1.8, 8.6 Hz), 7.95-7.91 (3H, m), 7.69 (1H, dd, J=4.6, 8.0 Hz), 7.38 (2H, t, J=8.8 Hz), 5.98 (1H, t, J=6.5 Hz), 4.88-4.78 (2H, m), 1.18 (9H, s). m/z (ES+) 497 [MH+].

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-7c53a78bd4e3466eb174cd3672ed309e
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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