Acetic Acid → N-[3-Methyl-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl]methylaniline

HRID 1501381Notes

Reaction equation

HRID 1501381 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]=O)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:16]=[CH:17][C:10]=23)[N:3]=1.C(Cl)Cl.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[CH3:1][C:2]1[C:6]([CH2:7][NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:16]=[CH:17][C:10]=23)[N:3]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6115Aniline2×HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 574775653-methyl-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 66597377N-[3-Methyl-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl]methylanilineYield 70%

Procedure

A solution of 3-methyl-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazole-4-carbaldehyde (0.025 g, 0.000070 mol) and aniline (1M in DCM, 0.070 mL), in DCM (1 mL, 0.02 mol) was stirred for 1 min. Acetic acid (20 μL, 0.0004 mol), aniline (1M in DCM, 140 μL) and sodium triacetoxyborohydride (0.022 g, 0.00010 mol) were added. The reaction was stirred overnight and partitioned between DCM and sat. NaHCO3, washed with brine. The organic phase was dried and evaporated to give 21 mg of a product as a pale orange glass (70% yield).

Workup

  1. custompartitioned between DCM and sat. NaHCO3
  2. washwashed with brine
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-91653830ee1047e094244fe841d0e6b9
Source dataset
uspto-grants-2015_12
Patent number
US09206187B2

Reaction notes

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