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Triethylamine → HCID 21099519, compound

HRID 1351655
Notes
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Reaction equation

HRID 1351655 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:15]([CH:18]=1)[CH:16]=O.Cl.[CH3:29][NH:30][CH3:31].C(N(CC)CC)C.C([BH3-])#N.[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:15]([CH:18]=1)[CH2:16][N:30]([CH3:31])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 21099516HCID 21099516, compound

Product 1

HCID 21099519HCID 21099519, compound

Reagents, catalysts & solvents 2

HCID 11026
Titanium isopropoxide
Catalyst
HCID 702EthanolSolvent

Procedure

A solution of 5-[(E)-2-(2,4-difluorophenyl)vinyl]-2-(phenylsulfonyl)benzaldehyde (prepared from Example 58 according to the method of Example 50 Step 1, 100 mg, 0.26 mmol), dimethylamine hydrochloride (50 mg, 0.62 mmol), titanium(IV) isopropoxide (0.2 mL, 0.62 mmol) and triethylamine (0.1 mL, 0.62 mmol) in ethanol (2 mL) was stirred at room temperature overnight. Sodium cyanoborohydride (35 mg, 0.56 mmol) was added and the reaction stirred for a further 3 hours. The solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 0–3% methanol/dichloromethane, to give the title compound as a white solid. δH (360 MHz, d6 DMSO): 8.12 (1H, d, J=8.2 Hz), 7.93–7.81 (5H, m), 7.68–7.56 (3H, m), 7.38 (2H, s), 7.33–7.27 (1H, m), 7.14 (1H, td, J=2.4, 8.5 Hz), 3.57 (2H, s), 1.88 (6H, s). m/z (ES+) 414 [MH+].

Workup

  1. stirringthe reaction stirred for a further 3 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with 0–3% methanol/dichloromethane

Sources & evidence

ORD record
ord-57a1a332dde847099a74aaa7e1acbcd5
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