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Water → HCID 21099479, compound

HRID 1351693
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Reaction equation

HRID 1351693 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[CH:22]=O)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[CH3:28][C:29]([S:32]([NH2:34])=[O:33])([CH3:31])[CH3:30].[BH4-].[Na+].O>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.ClCCl>[CH3:28][C:29]([S:32]([NH:34][CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=1[S:17]([C:14]1[CH:13]=[CH:12][C:11](/[CH:10]=[CH:9]/[C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][CH:2]=2)=[CH:16][CH:15]=1)(=[O:18])=[O:19])=[O:33])([CH3:31])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 4311764Sodium borohydrideHCID 21099432HCID 21099432, compound

Product 1

HCID 21099479HCID 21099479, compound

Reagents, catalysts & solvents 3

HCID 76524
Titanium tetraethoxide
Catalyst
HCID 6344DichloromethaneSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzaldehyde (Example 176, 500 mg, 1.44 mmol), 2-methyl-2-propanesulfinamide (192 mg, 1.58 mmol) and titanium(IV) ethoxide (0.6 mL, 2.88 mmol) in tetrahydrofuran (7 mL) was heated to reflux for 4 hours. The cooled reaction mixture was partitioned between ethyl acetate and brine. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was taken up in methanol/dichloromethane (3:1, 16 mL) and sodium borohydride (424 mg, 8.64 mmol) added portionwise. After stirring at room temperature for 10 minutes, water and dichloromethane were added. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 50–90% ethyl acetate/isohexane, followed by recrystallisation to give the title compound as a white solid. δH (500 MHz, d6 DMSO): 8.11 (1H, d, J=7.8 Hz), 7.84–7.80 (4H, m), 7.73–7.66 (4H, m), 7.59–7.57 (1H, m), 7.45 (1H, d, J=16.4 Hz), 7.30 (1H, d, J=16.5 Hz), 7.23 (2H, t, J=8.8 Hz), 5.78 (1H, t, J=6.4 Hz), 4.45–4.35 (2H, m), 1.07 (9H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customThe cooled reaction mixture
  4. customwas partitioned between ethyl acetate and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated in vacuo
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica
  10. washeluting with 50–90% ethyl acetate/isohexane
  11. customfollowed by recrystallisation

Sources & evidence

ORD record
ord-cc6c866be6e54ff9954ff9947becbf50
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217740B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes