Dimethylamine → 1-(3-(4-(1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)phenyl)-N,N-dimethylmethanamine

HRID 28957Notes

Reaction equation

HRID 28957 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[N:21]([S:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)(=[O:34])=[O:33])[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=5)=[CH:23][C:16]=34)=[CH:13][N:12]([CH2:41][CH3:42])[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:43][NH:44][CH3:45].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[N:21]([S:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)(=[O:34])=[O:33])[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:44]([CH3:45])[CH3:43])[CH:25]=5)=[CH:23][C:16]=34)=[CH:13][N:12]([CH2:41][CH3:42])[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 716509203-(4-(1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 689990361-(3-(4-(1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)phenyl)-N,N-dimethylmethanamineYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-[3-(4-nitrophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-(3-formylphenyl)-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine (1.3 mmol) in tetrahydrofuran (20 mL) was added a solution of 2 M dimethylamine in tetrahydrofuran (2.0 mmol) followed by sodium triacetoxyborohydride (1.9 mmol). The reaction was stirred at room temperature for 4 h and concentrated to dryness under vacuum. The residue was taken up in ethyl acetate, washed with brine, dried (sodium sulfate), filtered, and evaporated under vacuum. Purification by flash chromatography on silica gel (0-5% (5% ammonium hydroxide, methanol)/methylene chloride) gave the title compound as a yellow solid (87%). ESMS [M+H]+: 607.4

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customPurification by flash chromatography on silica gel (0-5% (5% ammonium hydroxide, methanol)/methylene chloride)

Sources & evidence

ORD record
ord-a45393fa69a34d3587d259f8d1aaff04
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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